<?xml version="1.0" encoding="UTF-8"?>

<!--XBRL Document Created with Wdesk from Workiva-->
<!--Copyright 2022 Workiva-->
<!--r:773e665a-ad09-4176-9bb0-8ef562c9e788,g:c1e8a3ec-d8bc-492c-9881-168757a4591f-->
<link:linkbase xmlns:link="http://www.xbrl.org/2003/linkbase" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:schemaLocation="http://www.xbrl.org/2003/linkbase http://www.xbrl.org/2003/xbrl-linkbase-2003-12-31.xsd">
  <link:roleRef roleURI="http://upwork.com/role/CONDENSEDCONSOLIDATEDBALANCESHEETS" xlink:type="simple" xlink:href="upwk-20220930.xsd#CONDENSEDCONSOLIDATEDBALANCESHEETS"/>
  <link:calculationLink xlink:role="http://upwork.com/role/CONDENSEDCONSOLIDATEDBALANCESHEETS" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsCurrent_4b07eeac-fd49-45fe-ba86-c5f3bfd29766" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AssetsCurrent"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_662051b1-1b3c-47b9-8256-b8d72310f565" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CashAndCashEquivalentsAtCarryingValue"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_4b07eeac-fd49-45fe-ba86-c5f3bfd29766" xlink:to="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_662051b1-1b3c-47b9-8256-b8d72310f565" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_EscrowDeposit_a55d89a7-f6d3-4197-8919-ba9ce7fae8c0" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_EscrowDeposit"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_4b07eeac-fd49-45fe-ba86-c5f3bfd29766" xlink:to="loc_us-gaap_EscrowDeposit_a55d89a7-f6d3-4197-8919-ba9ce7fae8c0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsReceivableNetCurrent_114852fc-0289-4ff7-a0b5-fdeabd26ec04" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccountsReceivableNetCurrent"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_4b07eeac-fd49-45fe-ba86-c5f3bfd29766" xlink:to="loc_us-gaap_AccountsReceivableNetCurrent_114852fc-0289-4ff7-a0b5-fdeabd26ec04" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_MarketableSecuritiesCurrent_507b7fdf-c71a-4f93-b23c-90b98d990c54" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_MarketableSecuritiesCurrent"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_4b07eeac-fd49-45fe-ba86-c5f3bfd29766" xlink:to="loc_us-gaap_MarketableSecuritiesCurrent_507b7fdf-c71a-4f93-b23c-90b98d990c54" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PrepaidExpenseAndOtherAssetsCurrent_124c21d7-c06c-4f71-982b-e99644364bc0" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PrepaidExpenseAndOtherAssetsCurrent"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_AssetsCurrent_4b07eeac-fd49-45fe-ba86-c5f3bfd29766" xlink:to="loc_us-gaap_PrepaidExpenseAndOtherAssetsCurrent_124c21d7-c06c-4f71-982b-e99644364bc0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Assets_4b61dc26-df3e-48d7-92a4-f7d9e6af5e47" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Assets"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Goodwill_b1cf79dd-ff56-4018-adfe-03a19b340005" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Goodwill"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_4b61dc26-df3e-48d7-92a4-f7d9e6af5e47" xlink:to="loc_us-gaap_Goodwill_b1cf79dd-ff56-4018-adfe-03a19b340005" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseRightOfUseAsset_5ffbcb51-5ad8-4c4f-b847-5875845deb39" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeaseRightOfUseAsset"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_4b61dc26-df3e-48d7-92a4-f7d9e6af5e47" xlink:to="loc_us-gaap_OperatingLeaseRightOfUseAsset_5ffbcb51-5ad8-4c4f-b847-5875845deb39" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetsCurrent_6674b93c-7b87-4fc8-acdf-76276ab30490" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AssetsCurrent"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_4b61dc26-df3e-48d7-92a4-f7d9e6af5e47" xlink:to="loc_us-gaap_AssetsCurrent_6674b93c-7b87-4fc8-acdf-76276ab30490" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherAssetsNoncurrent_ac699346-5315-4a59-8672-a6491de16877" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherAssetsNoncurrent"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_4b61dc26-df3e-48d7-92a4-f7d9e6af5e47" xlink:to="loc_us-gaap_OtherAssetsNoncurrent_ac699346-5315-4a59-8672-a6491de16877" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentNet_367f12c7-99f9-446a-b68a-ff0449ab335d" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertyPlantAndEquipmentNet"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Assets_4b61dc26-df3e-48d7-92a4-f7d9e6af5e47" xlink:to="loc_us-gaap_PropertyPlantAndEquipmentNet_367f12c7-99f9-446a-b68a-ff0449ab335d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities_73426acd-e59b-44da-85fd-f49e8944ddd1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Liabilities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherLiabilitiesNoncurrent_f0f347cc-3aa9-429f-81cb-9cfc24723081" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherLiabilitiesNoncurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_73426acd-e59b-44da-85fd-f49e8944ddd1" xlink:to="loc_us-gaap_OtherLiabilitiesNoncurrent_f0f347cc-3aa9-429f-81cb-9cfc24723081" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtNoncurrent_8dd04326-1ffc-454d-b381-04bb1e809c54" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LongTermDebtNoncurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_73426acd-e59b-44da-85fd-f49e8944ddd1" xlink:to="loc_us-gaap_LongTermDebtNoncurrent_8dd04326-1ffc-454d-b381-04bb1e809c54" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiabilityNoncurrent_a8dbe060-cb31-40c0-b484-191f3ca8269c" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeaseLiabilityNoncurrent"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_73426acd-e59b-44da-85fd-f49e8944ddd1" xlink:to="loc_us-gaap_OperatingLeaseLiabilityNoncurrent_a8dbe060-cb31-40c0-b484-191f3ca8269c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesCurrent_ee6b9363-1937-4df2-bced-8aad69ffdf4d" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilitiesCurrent"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_Liabilities_73426acd-e59b-44da-85fd-f49e8944ddd1" xlink:to="loc_us-gaap_LiabilitiesCurrent_ee6b9363-1937-4df2-bced-8aad69ffdf4d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity_fa07b78a-ecac-46b8-bf99-961cde347352" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StockholdersEquity"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_48f88869-3ff0-415a-8ac6-09aad39b3930" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_fa07b78a-ecac-46b8-bf99-961cde347352" xlink:to="loc_us-gaap_AccumulatedOtherComprehensiveIncomeLossNetOfTax_48f88869-3ff0-415a-8ac6-09aad39b3930" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RetainedEarningsAccumulatedDeficit_5e57168b-ce64-4ccd-8ecf-fd07034542d2" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RetainedEarningsAccumulatedDeficit"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_fa07b78a-ecac-46b8-bf99-961cde347352" xlink:to="loc_us-gaap_RetainedEarningsAccumulatedDeficit_5e57168b-ce64-4ccd-8ecf-fd07034542d2" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommonStockValue_340c3509-d981-4f6b-aec0-cfa099ab3c34" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommonStockValue"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_fa07b78a-ecac-46b8-bf99-961cde347352" xlink:to="loc_us-gaap_CommonStockValue_340c3509-d981-4f6b-aec0-cfa099ab3c34" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AdditionalPaidInCapitalCommonStock_2f34615e-a62a-4714-8fe4-71d9df47c2f7" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AdditionalPaidInCapitalCommonStock"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_StockholdersEquity_fa07b78a-ecac-46b8-bf99-961cde347352" xlink:to="loc_us-gaap_AdditionalPaidInCapitalCommonStock_2f34615e-a62a-4714-8fe4-71d9df47c2f7" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesCurrent_ac0d073b-2b87-49c2-8c52-9eec4d710b28" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilitiesCurrent"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ContractWithCustomerLiabilityCurrent_962b687b-a9e3-45a4-b475-f097a919ffce" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ContractWithCustomerLiabilityCurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_ac0d073b-2b87-49c2-8c52-9eec4d710b28" xlink:to="loc_us-gaap_ContractWithCustomerLiabilityCurrent_962b687b-a9e3-45a4-b475-f097a919ffce" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccountsPayableCurrent_b745a828-1d41-4162-a211-b690a838f220" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccountsPayableCurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_ac0d073b-2b87-49c2-8c52-9eec4d710b28" xlink:to="loc_us-gaap_AccountsPayableCurrent_b745a828-1d41-4162-a211-b690a838f220" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_upwk_AccruedExpensesAndOtherCurrentLiabilities_f1968b3a-1171-4c0e-b521-3e55cd2a6edf" xlink:href="upwk-20220930.xsd#upwk_AccruedExpensesAndOtherCurrentLiabilities"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_ac0d073b-2b87-49c2-8c52-9eec4d710b28" xlink:to="loc_upwk_AccruedExpensesAndOtherCurrentLiabilities_f1968b3a-1171-4c0e-b521-3e55cd2a6edf" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_upwk_EscrowFundsPayable_19fbb5ff-10a1-4d17-8639-bf2c2948ca1c" xlink:href="upwk-20220930.xsd#upwk_EscrowFundsPayable"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesCurrent_ac0d073b-2b87-49c2-8c52-9eec4d710b28" xlink:to="loc_upwk_EscrowFundsPayable_19fbb5ff-10a1-4d17-8639-bf2c2948ca1c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LiabilitiesAndStockholdersEquity_42223a60-1211-481b-a79b-89c90c27a046" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LiabilitiesAndStockholdersEquity"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_Liabilities_75d5fb67-f959-4849-946e-39cd576da4e0" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_Liabilities"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_42223a60-1211-481b-a79b-89c90c27a046" xlink:to="loc_us-gaap_Liabilities_75d5fb67-f959-4849-946e-39cd576da4e0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CommitmentsAndContingencies_3a342328-98e8-4315-9673-7124335c266d" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CommitmentsAndContingencies"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_42223a60-1211-481b-a79b-89c90c27a046" xlink:to="loc_us-gaap_CommitmentsAndContingencies_3a342328-98e8-4315-9673-7124335c266d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_StockholdersEquity_1e5ca39b-2190-4dff-a4d2-31907f71cc41" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_StockholdersEquity"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LiabilitiesAndStockholdersEquity_42223a60-1211-481b-a79b-89c90c27a046" xlink:to="loc_us-gaap_StockholdersEquity_1e5ca39b-2190-4dff-a4d2-31907f71cc41" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://upwork.com/role/CONDENSEDCONSOLIDATEDSTATEMENTSOFOPERATIONSANDCOMPREHENSIVELOSS" xlink:type="simple" xlink:href="upwk-20220930.xsd#CONDENSEDCONSOLIDATEDSTATEMENTSOFOPERATIONSANDCOMPREHENSIVELOSS"/>
  <link:calculationLink xlink:role="http://upwork.com/role/CONDENSEDCONSOLIDATEDSTATEMENTSOFOPERATIONSANDCOMPREHENSIVELOSS" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingExpenses_3bfd2b1f-6d7c-46ae-9d51-e1c9bdd23b8d" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingExpenses"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ResearchAndDevelopmentExpense_7aedfb80-d717-4d97-a673-1925d162ce2c" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ResearchAndDevelopmentExpense"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_3bfd2b1f-6d7c-46ae-9d51-e1c9bdd23b8d" xlink:to="loc_us-gaap_ResearchAndDevelopmentExpense_7aedfb80-d717-4d97-a673-1925d162ce2c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_SellingAndMarketingExpense_5271905c-c186-452d-9a60-ddff96871737" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_SellingAndMarketingExpense"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_3bfd2b1f-6d7c-46ae-9d51-e1c9bdd23b8d" xlink:to="loc_us-gaap_SellingAndMarketingExpense_5271905c-c186-452d-9a60-ddff96871737" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GeneralAndAdministrativeExpense_5a08ef40-8108-47d1-84e2-8292670d2b6e" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GeneralAndAdministrativeExpense"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_3bfd2b1f-6d7c-46ae-9d51-e1c9bdd23b8d" xlink:to="loc_us-gaap_GeneralAndAdministrativeExpense_5a08ef40-8108-47d1-84e2-8292670d2b6e" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_upwk_ProvisionForTransactionLosses_48009747-2d26-4f30-ad3f-7c7e8f2ac740" xlink:href="upwk-20220930.xsd#upwk_ProvisionForTransactionLosses"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingExpenses_3bfd2b1f-6d7c-46ae-9d51-e1c9bdd23b8d" xlink:to="loc_upwk_ProvisionForTransactionLosses_48009747-2d26-4f30-ad3f-7c7e8f2ac740" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GrossProfit_4496db80-f989-4a18-ac2e-1e274b5933aa" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GrossProfit"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax_00f2bde6-fba4-4192-a511-c172249f2df6" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_GrossProfit_4496db80-f989-4a18-ac2e-1e274b5933aa" xlink:to="loc_us-gaap_RevenueFromContractWithCustomerExcludingAssessedTax_00f2bde6-fba4-4192-a511-c172249f2df6" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CostOfGoodsAndServicesSold_5eca5354-5a3b-4626-aaf5-7445a1930801" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CostOfGoodsAndServicesSold"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_GrossProfit_4496db80-f989-4a18-ac2e-1e274b5933aa" xlink:to="loc_us-gaap_CostOfGoodsAndServicesSold_5eca5354-5a3b-4626-aaf5-7445a1930801" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingIncomeLoss_f502b20f-4bde-4094-994c-3b3292e83b0c" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingIncomeLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_GrossProfit_99d5ae7f-d6e9-459f-bef0-6c3ccde388b6" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_GrossProfit"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingIncomeLoss_f502b20f-4bde-4094-994c-3b3292e83b0c" xlink:to="loc_us-gaap_GrossProfit_99d5ae7f-d6e9-459f-bef0-6c3ccde388b6" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingExpenses_4ef06111-cac9-4967-9328-0ef63c4b938a" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingExpenses"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_OperatingIncomeLoss_f502b20f-4bde-4094-994c-3b3292e83b0c" xlink:to="loc_us-gaap_OperatingExpenses_4ef06111-cac9-4967-9328-0ef63c4b938a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_17887b33-4392-4b83-a79a-81cc7df2acd0" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingIncomeLoss_919698bf-d46a-491b-9d55-6521d0f8fc59" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingIncomeLoss"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_17887b33-4392-4b83-a79a-81cc7df2acd0" xlink:to="loc_us-gaap_OperatingIncomeLoss_919698bf-d46a-491b-9d55-6521d0f8fc59" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_InterestExpense_23eaf981-6440-4490-83b0-67c091a680ab" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_InterestExpense"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_17887b33-4392-4b83-a79a-81cc7df2acd0" xlink:to="loc_us-gaap_InterestExpense_23eaf981-6440-4490-83b0-67c091a680ab" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherNonoperatingIncomeExpense_4eda8c5b-5712-49b8-9a46-01a54f3b207f" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherNonoperatingIncomeExpense"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_17887b33-4392-4b83-a79a-81cc7df2acd0" xlink:to="loc_us-gaap_OtherNonoperatingIncomeExpense_4eda8c5b-5712-49b8-9a46-01a54f3b207f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_5415732e-148e-4f04-a5ba-a1f3d5f125ff" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetIncomeLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_96468605-fab3-471e-843e-0892bb8f4cfd" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_5415732e-148e-4f04-a5ba-a1f3d5f125ff" xlink:to="loc_us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesExtraordinaryItemsNoncontrollingInterest_96468605-fab3-471e-843e-0892bb8f4cfd" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncomeTaxExpenseBenefit_7d5bde11-14c9-4f33-981b-0994f300c47d" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncomeTaxExpenseBenefit"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetIncomeLoss_5415732e-148e-4f04-a5ba-a1f3d5f125ff" xlink:to="loc_us-gaap_IncomeTaxExpenseBenefit_7d5bde11-14c9-4f33-981b-0994f300c47d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ComprehensiveIncomeNetOfTax_3a593dc0-9127-440f-a7b0-ca218d91a488" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ComprehensiveIncomeNetOfTax"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherComprehensiveIncomeAvailableforsaleSecuritiesAdjustmentNetOfTaxPortionAttributableToParent_f87ce2ea-7b8f-413d-8dd0-63d0ccc522dc" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherComprehensiveIncomeAvailableforsaleSecuritiesAdjustmentNetOfTaxPortionAttributableToParent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTax_3a593dc0-9127-440f-a7b0-ca218d91a488" xlink:to="loc_us-gaap_OtherComprehensiveIncomeAvailableforsaleSecuritiesAdjustmentNetOfTaxPortionAttributableToParent_f87ce2ea-7b8f-413d-8dd0-63d0ccc522dc" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetIncomeLoss_802772ae-de68-4fdf-aa5f-bcf7f5dd6e54" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetIncomeLoss"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_ComprehensiveIncomeNetOfTax_3a593dc0-9127-440f-a7b0-ca218d91a488" xlink:to="loc_us-gaap_NetIncomeLoss_802772ae-de68-4fdf-aa5f-bcf7f5dd6e54" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://upwork.com/role/CONDENSEDCONSOLIDATEDSTATEMENTSOFCASHFLOWS" xlink:type="simple" xlink:href="upwk-20220930.xsd#CONDENSEDCONSOLIDATEDSTATEMENTSOFCASHFLOWS"/>
  <link:calculationLink xlink:role="http://upwork.com/role/CONDENSEDCONSOLIDATEDSTATEMENTSOFCASHFLOWS" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_ea8d7c0f-6664-41ec-8773-f97ddbac9903" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromStockPlans_d897ffb1-c038-4bf4-b4a1-27e5f186a5bf" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromStockPlans"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_ea8d7c0f-6664-41ec-8773-f97ddbac9903" xlink:to="loc_us-gaap_ProceedsFromStockPlans_d897ffb1-c038-4bf4-b4a1-27e5f186a5bf" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RepaymentsOfDebt_01f80175-2405-46d2-b7c1-a347dac03766" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RepaymentsOfDebt"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_ea8d7c0f-6664-41ec-8773-f97ddbac9903" xlink:to="loc_us-gaap_RepaymentsOfDebt_01f80175-2405-46d2-b7c1-a347dac03766" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_upwk_ProceedsFromExercisesOfStockOptionsAndCommonStockWarrant_d0fbebc4-4fc5-4348-bbab-9b82577e18c0" xlink:href="upwk-20220930.xsd#upwk_ProceedsFromExercisesOfStockOptionsAndCommonStockWarrant"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_ea8d7c0f-6664-41ec-8773-f97ddbac9903" xlink:to="loc_upwk_ProceedsFromExercisesOfStockOptionsAndCommonStockWarrant_d0fbebc4-4fc5-4348-bbab-9b82577e18c0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_upwk_ChangesInEscrowFundsPayable_d7eee4e3-8512-45f7-bbfe-b3450a22df6d" xlink:href="upwk-20220930.xsd#upwk_ChangesInEscrowFundsPayable"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_ea8d7c0f-6664-41ec-8773-f97ddbac9903" xlink:to="loc_upwk_ChangesInEscrowFundsPayable_d7eee4e3-8512-45f7-bbfe-b3450a22df6d" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsOfDebtIssuanceCosts_702c7e06-070b-418b-9123-f3437737c742" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsOfDebtIssuanceCosts"/>
    <link:calculationArc order="5" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_ea8d7c0f-6664-41ec-8773-f97ddbac9903" xlink:to="loc_us-gaap_PaymentsOfDebtIssuanceCosts_702c7e06-070b-418b-9123-f3437737c742" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromConvertibleDebt_13153712-2303-467a-8ac2-d49434486d84" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromConvertibleDebt"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_ea8d7c0f-6664-41ec-8773-f97ddbac9903" xlink:to="loc_us-gaap_ProceedsFromConvertibleDebt_13153712-2303-467a-8ac2-d49434486d84" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_upwk_PaymentsForPurchaseOfCappedCallsOnConvertibleNotes_25038f67-b005-454b-a04b-df4f4bc256fa" xlink:href="upwk-20220930.xsd#upwk_PaymentsForPurchaseOfCappedCallsOnConvertibleNotes"/>
    <link:calculationArc order="7" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_ea8d7c0f-6664-41ec-8773-f97ddbac9903" xlink:to="loc_upwk_PaymentsForPurchaseOfCappedCallsOnConvertibleNotes_25038f67-b005-454b-a04b-df4f4bc256fa" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_60636712-b8ea-4afa-8218-bc00862aeea5" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProvisionForLoanLeaseAndOtherLosses_82f0d441-ee49-4f50-bc99-b2a580f45038" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProvisionForLoanLeaseAndOtherLosses"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_60636712-b8ea-4afa-8218-bc00862aeea5" xlink:to="loc_us-gaap_ProvisionForLoanLeaseAndOtherLosses_82f0d441-ee49-4f50-bc99-b2a580f45038" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_upwk_IncreaseDecreaseInCommonStockWarrant_b24ab10d-813b-4304-adf1-09acf5f3ff7c" xlink:href="upwk-20220930.xsd#upwk_IncreaseDecreaseInCommonStockWarrant"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_60636712-b8ea-4afa-8218-bc00862aeea5" xlink:to="loc_upwk_IncreaseDecreaseInCommonStockWarrant_b24ab10d-813b-4304-adf1-09acf5f3ff7c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseRightOfUseAssetAmortizationExpense_e782fa2c-4e5f-4c27-aec0-5b2a5d3b6013" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeaseRightOfUseAssetAmortizationExpense"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_60636712-b8ea-4afa-8218-bc00862aeea5" xlink:to="loc_us-gaap_OperatingLeaseRightOfUseAssetAmortizationExpense_e782fa2c-4e5f-4c27-aec0-5b2a5d3b6013" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInAccountsReceivable_4b2c3145-0809-48aa-9465-5f705c94f602" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInAccountsReceivable"/>
    <link:calculationArc order="4" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_60636712-b8ea-4afa-8218-bc00862aeea5" xlink:to="loc_us-gaap_IncreaseDecreaseInAccountsReceivable_4b2c3145-0809-48aa-9465-5f705c94f602" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ShareBasedCompensation_4083dc4a-3ba6-4cf9-bf64-632fc988b905" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ShareBasedCompensation"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_60636712-b8ea-4afa-8218-bc00862aeea5" xlink:to="loc_us-gaap_ShareBasedCompensation_4083dc4a-3ba6-4cf9-bf64-632fc988b905" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInAccountsPayable_fcce2fff-5261-4a15-974b-b740b1355968" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInAccountsPayable"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_60636712-b8ea-4afa-8218-bc00862aeea5" xlink:to="loc_us-gaap_IncreaseDecreaseInAccountsPayable_fcce2fff-5261-4a15-974b-b740b1355968" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInAccruedLiabilitiesAndOtherOperatingLiabilities_1f2301ad-db31-4c74-9f1b-54ebdb939c83" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInAccruedLiabilitiesAndOtherOperatingLiabilities"/>
    <link:calculationArc order="7" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_60636712-b8ea-4afa-8218-bc00862aeea5" xlink:to="loc_us-gaap_IncreaseDecreaseInAccruedLiabilitiesAndOtherOperatingLiabilities_1f2301ad-db31-4c74-9f1b-54ebdb939c83" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_upwk_IncreaseDecreaseOperatingLeaseLiability_32492f3a-f24c-4f89-90ef-afcb3e8e4ab5" xlink:href="upwk-20220930.xsd#upwk_IncreaseDecreaseOperatingLeaseLiability"/>
    <link:calculationArc order="8" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_60636712-b8ea-4afa-8218-bc00862aeea5" xlink:to="loc_upwk_IncreaseDecreaseOperatingLeaseLiability_32492f3a-f24c-4f89-90ef-afcb3e8e4ab5" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccretionAmortizationOfDiscountsAndPremiumsInvestments_dec1a103-1bc0-45cb-9bb1-ba937dc0ddba" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccretionAmortizationOfDiscountsAndPremiumsInvestments"/>
    <link:calculationArc order="9" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_60636712-b8ea-4afa-8218-bc00862aeea5" xlink:to="loc_us-gaap_AccretionAmortizationOfDiscountsAndPremiumsInvestments_dec1a103-1bc0-45cb-9bb1-ba937dc0ddba" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInPrepaidDeferredExpenseAndOtherAssets_27280edb-3745-46ae-82de-39bc4ba00bc8" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInPrepaidDeferredExpenseAndOtherAssets"/>
    <link:calculationArc order="10" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_60636712-b8ea-4afa-8218-bc00862aeea5" xlink:to="loc_us-gaap_IncreaseDecreaseInPrepaidDeferredExpenseAndOtherAssets_27280edb-3745-46ae-82de-39bc4ba00bc8" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_upwk_DepreciationAndAmortizationExcludingAmortizationOfFinancingCosts_f3a0106e-f1cb-4074-95b8-c69c7af648e7" xlink:href="upwk-20220930.xsd#upwk_DepreciationAndAmortizationExcludingAmortizationOfFinancingCosts"/>
    <link:calculationArc order="11" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_60636712-b8ea-4afa-8218-bc00862aeea5" xlink:to="loc_upwk_DepreciationAndAmortizationExcludingAmortizationOfFinancingCosts_f3a0106e-f1cb-4074-95b8-c69c7af648e7" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AssetImpairmentCharges_32304117-2330-424b-bebc-3df81eca8952" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AssetImpairmentCharges"/>
    <link:calculationArc order="12" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_60636712-b8ea-4afa-8218-bc00862aeea5" xlink:to="loc_us-gaap_AssetImpairmentCharges_32304117-2330-424b-bebc-3df81eca8952" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProfitLoss_b2bf951a-97d5-4f36-9b51-81322bd1bc43" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProfitLoss"/>
    <link:calculationArc order="13" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_60636712-b8ea-4afa-8218-bc00862aeea5" xlink:to="loc_us-gaap_ProfitLoss_b2bf951a-97d5-4f36-9b51-81322bd1bc43" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AmortizationOfFinancingCosts_6bac9d75-2456-451d-a87e-738fa198e4a0" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AmortizationOfFinancingCosts"/>
    <link:calculationArc order="14" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_60636712-b8ea-4afa-8218-bc00862aeea5" xlink:to="loc_us-gaap_AmortizationOfFinancingCosts_6bac9d75-2456-451d-a87e-738fa198e4a0" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_IncreaseDecreaseInDeferredRevenue_1e03dfcb-427e-443d-a7bd-7396dac1083a" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_IncreaseDecreaseInDeferredRevenue"/>
    <link:calculationArc order="15" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_60636712-b8ea-4afa-8218-bc00862aeea5" xlink:to="loc_us-gaap_IncreaseDecreaseInDeferredRevenue_1e03dfcb-427e-443d-a7bd-7396dac1083a" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_cf0a3443-c0c5-49d6-a7e4-458eb6ca7436" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_ab9b823c-add0-478c-8922-f1727a010515" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsToAcquirePropertyPlantAndEquipment"/>
    <link:calculationArc order="1" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_cf0a3443-c0c5-49d6-a7e4-458eb6ca7436" xlink:to="loc_us-gaap_PaymentsToAcquirePropertyPlantAndEquipment_ab9b823c-add0-478c-8922-f1727a010515" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities_355aa332-88f4-465e-b8f3-b087c24139c6" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_cf0a3443-c0c5-49d6-a7e4-458eb6ca7436" xlink:to="loc_us-gaap_ProceedsFromSaleAndMaturityOfMarketableSecurities_355aa332-88f4-465e-b8f3-b087c24139c6" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToAcquireMarketableSecurities_c01c0e4b-5054-4617-9d39-cdd0e9044e6e" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsToAcquireMarketableSecurities"/>
    <link:calculationArc order="3" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_cf0a3443-c0c5-49d6-a7e4-458eb6ca7436" xlink:to="loc_us-gaap_PaymentsToAcquireMarketableSecurities_c01c0e4b-5054-4617-9d39-cdd0e9044e6e" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PaymentsToDevelopSoftware_a7d6fcdf-3bec-462e-855c-29e2776e9203" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PaymentsToDevelopSoftware"/>
    <link:calculationArc order="4" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_cf0a3443-c0c5-49d6-a7e4-458eb6ca7436" xlink:to="loc_us-gaap_PaymentsToDevelopSoftware_a7d6fcdf-3bec-462e-855c-29e2776e9203" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_0da2b6e4-15e4-42fd-b981-f3cbe8c99cd3" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_583f53a2-58c1-4dd2-88b1-d57330c7117f" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInOperatingActivities"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_0da2b6e4-15e4-42fd-b981-f3cbe8c99cd3" xlink:to="loc_us-gaap_NetCashProvidedByUsedInOperatingActivities_583f53a2-58c1-4dd2-88b1-d57330c7117f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_8b1bad4b-77a4-4dc9-8c63-98ebb5f8dc9f" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInInvestingActivities"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_0da2b6e4-15e4-42fd-b981-f3cbe8c99cd3" xlink:to="loc_us-gaap_NetCashProvidedByUsedInInvestingActivities_8b1bad4b-77a4-4dc9-8c63-98ebb5f8dc9f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_e1ee730a-4f07-4ef5-a4ab-09bbacbf3f63" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_NetCashProvidedByUsedInFinancingActivities"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalentsPeriodIncreaseDecreaseIncludingExchangeRateEffect_0da2b6e4-15e4-42fd-b981-f3cbe8c99cd3" xlink:to="loc_us-gaap_NetCashProvidedByUsedInFinancingActivities_e1ee730a-4f07-4ef5-a4ab-09bbacbf3f63" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://upwork.com/role/FairValueMeasurementsandMarketableSecuritiesFinancialAssetsMeasuredatFairValueDetails" xlink:type="simple" xlink:href="upwk-20220930.xsd#FairValueMeasurementsandMarketableSecuritiesFinancialAssetsMeasuredatFairValueDetails"/>
  <link:calculationLink xlink:role="http://upwork.com/role/FairValueMeasurementsandMarketableSecuritiesFinancialAssetsMeasuredatFairValueDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss_38c8db62-425d-41a7-976e-42eb90e07ac1" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax_c63c89e0-aa44-4e61-9160-2f023d2cc7ef" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss_38c8db62-425d-41a7-976e-42eb90e07ac1" xlink:to="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedLossBeforeTax_c63c89e0-aa44-4e61-9160-2f023d2cc7ef" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_3ebf166e-ae0b-4d98-ab00-f953b41451a7" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss_38c8db62-425d-41a7-976e-42eb90e07ac1" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleExcludingAccruedInterest_3ebf166e-ae0b-4d98-ab00-f953b41451a7" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_0ba02cc8-9125-4bb9-a285-190b5cd326d9" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax"/>
    <link:calculationArc order="3" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleAmortizedCostExcludingAccruedInterestAfterAllowanceForCreditLoss_38c8db62-425d-41a7-976e-42eb90e07ac1" xlink:to="loc_us-gaap_AvailableForSaleDebtSecuritiesAccumulatedGrossUnrealizedGainBeforeTax_0ba02cc8-9125-4bb9-a285-190b5cd326d9" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://upwork.com/role/FairValueMeasurementsUnrealizedGainLossOnInvestmentsDetails" xlink:type="simple" xlink:href="upwk-20220930.xsd#FairValueMeasurementsUnrealizedGainLossOnInvestmentsDetails"/>
  <link:calculationLink xlink:role="http://upwork.com/role/FairValueMeasurementsUnrealizedGainLossOnInvestmentsDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_a421bd81-76e3-4aa1-bd5f-aa9363f085ae" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_282eee1b-61a7-4ea9-8d83-230a7a8c7438" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_a421bd81-76e3-4aa1-bd5f-aa9363f085ae" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12MonthsAccumulatedLoss_282eee1b-61a7-4ea9-8d83-230a7a8c7438" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_fc1208b2-6c72-4992-b06b-ddd710939d31" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPositionAccumulatedLoss_a421bd81-76e3-4aa1-bd5f-aa9363f085ae" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLongerAccumulatedLoss_fc1208b2-6c72-4992-b06b-ddd710939d31" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition_f5c5252f-456c-487f-9d79-557512785e89" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_9da186fd-ecc9-43d2-a096-af970c895595" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition_f5c5252f-456c-487f-9d79-557512785e89" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPosition12MonthsOrLonger_9da186fd-ecc9-43d2-a096-af970c895595" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months_f09df8ce-8e39-4635-9a6c-3cc0d7a6420d" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_DebtSecuritiesAvailableForSaleUnrealizedLossPosition_f5c5252f-456c-487f-9d79-557512785e89" xlink:to="loc_us-gaap_DebtSecuritiesAvailableForSaleContinuousUnrealizedLossPositionLessThan12Months_f09df8ce-8e39-4635-9a6c-3cc0d7a6420d" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://upwork.com/role/BalanceSheetComponentsCashandCashEquivalentsDetails" xlink:type="simple" xlink:href="upwk-20220930.xsd#BalanceSheetComponentsCashandCashEquivalentsDetails"/>
  <link:calculationLink xlink:role="http://upwork.com/role/BalanceSheetComponentsCashandCashEquivalentsDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_4b616091-f9fc-4e3a-b65c-92c034aace72" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_c1ea9366-2b35-4229-91e9-851e4c230d45" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_CashAndCashEquivalentsAtCarryingValue"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_4b616091-f9fc-4e3a-b65c-92c034aace72" xlink:to="loc_us-gaap_CashAndCashEquivalentsAtCarryingValue_c1ea9366-2b35-4229-91e9-851e4c230d45" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_upwk_FundsHeldInEscrowIncludingFundsInTransit_f81794b8-4f22-4c1d-adb8-c5a0ac936938" xlink:href="upwk-20220930.xsd#upwk_FundsHeldInEscrowIncludingFundsInTransit"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_4b616091-f9fc-4e3a-b65c-92c034aace72" xlink:to="loc_upwk_FundsHeldInEscrowIncludingFundsInTransit_f81794b8-4f22-4c1d-adb8-c5a0ac936938" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_RestrictedCash_4f8d1833-f08d-4ce2-a126-ddd2802f2a98" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_RestrictedCash"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_CashCashEquivalentsRestrictedCashAndRestrictedCashEquivalents_4b616091-f9fc-4e3a-b65c-92c034aace72" xlink:to="loc_us-gaap_RestrictedCash_4f8d1833-f08d-4ce2-a126-ddd2802f2a98" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://upwork.com/role/BalanceSheetComponentsPropertyandEquipmentNetDetails" xlink:type="simple" xlink:href="upwk-20220930.xsd#BalanceSheetComponentsPropertyandEquipmentNetDetails"/>
  <link:calculationLink xlink:role="http://upwork.com/role/BalanceSheetComponentsPropertyandEquipmentNetDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentNet_a73f4e0c-c37e-4641-bcad-529b67632fdb" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertyPlantAndEquipmentNet"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_PropertyPlantAndEquipmentGross_9c88bc44-da58-408e-90b6-20a00a60a99f" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_PropertyPlantAndEquipmentGross"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentNet_a73f4e0c-c37e-4641-bcad-529b67632fdb" xlink:to="loc_us-gaap_PropertyPlantAndEquipmentGross_9c88bc44-da58-408e-90b6-20a00a60a99f" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment_05d87e32-20a2-4944-bdc5-02d78b5dd706" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_PropertyPlantAndEquipmentNet_a73f4e0c-c37e-4641-bcad-529b67632fdb" xlink:to="loc_us-gaap_AccumulatedDepreciationDepletionAndAmortizationPropertyPlantAndEquipment_05d87e32-20a2-4944-bdc5-02d78b5dd706" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://upwork.com/role/BalanceSheetComponentsAccruedExpensesandOtherCurrentLiabilitiesDetails" xlink:type="simple" xlink:href="upwk-20220930.xsd#BalanceSheetComponentsAccruedExpensesandOtherCurrentLiabilitiesDetails"/>
  <link:calculationLink xlink:role="http://upwork.com/role/BalanceSheetComponentsAccruedExpensesandOtherCurrentLiabilitiesDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_upwk_AccruedExpensesAndOtherCurrentLiabilities_3d5203f0-f672-40a0-b4ae-35244eeb34b9" xlink:href="upwk-20220930.xsd#upwk_AccruedExpensesAndOtherCurrentLiabilities"/>
    <link:loc xlink:type="locator" xlink:label="loc_upwk_AccruedIndirectTaxesCurrent_34a2bf93-356a-47e9-bf39-9f782e4f3585" xlink:href="upwk-20220930.xsd#upwk_AccruedIndirectTaxesCurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_upwk_AccruedExpensesAndOtherCurrentLiabilities_3d5203f0-f672-40a0-b4ae-35244eeb34b9" xlink:to="loc_upwk_AccruedIndirectTaxesCurrent_34a2bf93-356a-47e9-bf39-9f782e4f3585" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OtherAccruedLiabilitiesCurrent_bdcb7a16-1162-442c-bb1f-ba1cc11a5544" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OtherAccruedLiabilitiesCurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_upwk_AccruedExpensesAndOtherCurrentLiabilities_3d5203f0-f672-40a0-b4ae-35244eeb34b9" xlink:to="loc_us-gaap_OtherAccruedLiabilitiesCurrent_bdcb7a16-1162-442c-bb1f-ba1cc11a5544" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_upwk_AccruedPaymentProcessingFeesCurrent_348be225-32ff-4fed-8dad-929c61699650" xlink:href="upwk-20220930.xsd#upwk_AccruedPaymentProcessingFeesCurrent"/>
    <link:calculationArc order="3" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_upwk_AccruedExpensesAndOtherCurrentLiabilities_3d5203f0-f672-40a0-b4ae-35244eeb34b9" xlink:to="loc_upwk_AccruedPaymentProcessingFeesCurrent_348be225-32ff-4fed-8dad-929c61699650" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_OperatingLeaseLiabilityCurrent_6412dcdc-c0ac-4a70-b3fb-47fc2bfb5082" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_OperatingLeaseLiabilityCurrent"/>
    <link:calculationArc order="4" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_upwk_AccruedExpensesAndOtherCurrentLiabilities_3d5203f0-f672-40a0-b4ae-35244eeb34b9" xlink:to="loc_us-gaap_OperatingLeaseLiabilityCurrent_6412dcdc-c0ac-4a70-b3fb-47fc2bfb5082" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_upwk_AccruedCompensationAndRelatedBenefitsCurrent_6b1576bc-cae2-4fca-bcf6-29ba4999098c" xlink:href="upwk-20220930.xsd#upwk_AccruedCompensationAndRelatedBenefitsCurrent"/>
    <link:calculationArc order="5" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_upwk_AccruedExpensesAndOtherCurrentLiabilities_3d5203f0-f672-40a0-b4ae-35244eeb34b9" xlink:to="loc_upwk_AccruedCompensationAndRelatedBenefitsCurrent_6b1576bc-cae2-4fca-bcf6-29ba4999098c" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_upwk_AccruedVendorExpensesCurrent_7e5f3dd6-5cab-45e5-aadc-db8be02fb830" xlink:href="upwk-20220930.xsd#upwk_AccruedVendorExpensesCurrent"/>
    <link:calculationArc order="6" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_upwk_AccruedExpensesAndOtherCurrentLiabilities_3d5203f0-f672-40a0-b4ae-35244eeb34b9" xlink:to="loc_upwk_AccruedVendorExpensesCurrent_7e5f3dd6-5cab-45e5-aadc-db8be02fb830" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_upwk_AccruedFreelancerCostsCurrent_ee744609-b515-4a10-a8f8-4542723b28b0" xlink:href="upwk-20220930.xsd#upwk_AccruedFreelancerCostsCurrent"/>
    <link:calculationArc order="7" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_upwk_AccruedExpensesAndOtherCurrentLiabilities_3d5203f0-f672-40a0-b4ae-35244eeb34b9" xlink:to="loc_upwk_AccruedFreelancerCostsCurrent_ee744609-b515-4a10-a8f8-4542723b28b0" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://upwork.com/role/DebtSummaryofCarryingValueofDebtDetails" xlink:type="simple" xlink:href="upwk-20220930.xsd#DebtSummaryofCarryingValueofDebtDetails"/>
  <link:calculationLink xlink:role="http://upwork.com/role/DebtSummaryofCarryingValueofDebtDetails" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebt_d16c9bd6-02c0-4052-88d2-be99390580dd" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LongTermDebt"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtCurrent_8dfdcd9e-ffb7-484b-bc7b-4fd2f0f0e724" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LongTermDebtCurrent"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LongTermDebt_d16c9bd6-02c0-4052-88d2-be99390580dd" xlink:to="loc_us-gaap_LongTermDebtCurrent_8dfdcd9e-ffb7-484b-bc7b-4fd2f0f0e724" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebtNoncurrent_d62c6075-4f8b-4ed5-ae08-4043efc65545" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LongTermDebtNoncurrent"/>
    <link:calculationArc order="2" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LongTermDebt_d16c9bd6-02c0-4052-88d2-be99390580dd" xlink:to="loc_us-gaap_LongTermDebtNoncurrent_d62c6075-4f8b-4ed5-ae08-4043efc65545" xlink:type="arc"/>
  </link:calculationLink>
  <link:roleRef roleURI="http://upwork.com/role/DebtSummaryofCarryingValueofDebtDetails_1" xlink:type="simple" xlink:href="upwk-20220930.xsd#DebtSummaryofCarryingValueofDebtDetails_1"/>
  <link:calculationLink xlink:role="http://upwork.com/role/DebtSummaryofCarryingValueofDebtDetails_1" xlink:type="extended">
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_LongTermDebt_2e45eaa3-bf0e-4571-b5db-26ac9c84352b" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_LongTermDebt"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentCarryingAmount_4ca0475f-b584-4964-88d7-d09a1dbc3251" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentCarryingAmount"/>
    <link:calculationArc order="1" weight="1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LongTermDebt_2e45eaa3-bf0e-4571-b5db-26ac9c84352b" xlink:to="loc_us-gaap_DebtInstrumentCarryingAmount_4ca0475f-b584-4964-88d7-d09a1dbc3251" xlink:type="arc"/>
    <link:loc xlink:type="locator" xlink:label="loc_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet_df8a5a53-0fd5-49c3-a2da-5ba482bfe243" xlink:href="https://xbrl.fasb.org/us-gaap/2022/elts/us-gaap-2022.xsd#us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet"/>
    <link:calculationArc order="2" weight="-1.0" xlink:arcrole="http://www.xbrl.org/2003/arcrole/summation-item" xlink:from="loc_us-gaap_LongTermDebt_2e45eaa3-bf0e-4571-b5db-26ac9c84352b" xlink:to="loc_us-gaap_DebtInstrumentUnamortizedDiscountPremiumAndDebtIssuanceCostsNet_df8a5a53-0fd5-49c3-a2da-5ba482bfe243" xlink:type="arc"/>
  </link:calculationLink>
</link:linkbase>
