SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 20-F ☐REGISTRATION STATEMENT PURSUANT TO SECTION 12(b) OR 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 OR ☒ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December31, 2025 OR ☐TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 OR ☐SHELL COMPANY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Commission file number 001-31909 ASPEN INSURANCE HOLDINGS LIMITED (Exact name of registrant as specified in its charter) Bermuda (Jurisdiction of incorporation or organization) Waterloo House, 100 Pitts Bay Road, Pembroke, HM08, Bermuda (Address of principal executive offices) James A. Shea Executive Chairman and Chief Executive Officer Waterloo House, 100 Pitts Bay Road, Pembroke, HM08, Bermuda Telephone: +1 441-278 0400, Email: jshea@sompo-intl.com (Name, Telephone, E-mail and/or Facsimile Number and Address of Company Contact Person) If this report is an annual or transition report, indicate by check mark if the registrant is not required to file reports pursuant to Section 13 or Section 15(d) of the Act:Yes☐No☒ Indicate by check mark whether the registrant (1)has filed all reports required to be filed by Section13 or 15(d) of the Exchange Act of 1934 during the preceding 12months (or for such shorter periods that the registrant was required to file such reports), and (2)has been subject to such filing requirements for the past 90days.YesNo☐ Indicate by check mark whether the registrant has submitted electronically every Interactive Data File required to be submitted pursuant to Rule 405 of Regulation S-T(§232.405 of this chapter) during the preceding 12months (or for such shorter period that the registrant was required to submit such files).Yes☒No☐ Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, or an emerging growth company. See thedefinitions of “large accelerated filer,” “accelerated filer” and “emerging growth company” in Rule12b-2 of the Exchange Act.: ☐Accelerated filer☒Non-accelerated filer☐Emerging growth company If an emerging growth company that prepares its financial statements in accordance with U.S. GAAP, indicate by check mark if the registrant has elected not to use theextended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act.☐ Indicate by check mark whether the registrant has filed a report on and attestation to its management’s assessment of the effectiveness of its internal control overfinancial reporting under Section 404(b) of the Sarbanes-Oxley Act (15 U.S.C. 7262(b)) by the registered public accounting firm that prepared or issued its audit report.☒ If securities are registered pursuant to Section 12(b) of the Act, indicate by check mark whether the financial statements of the registrant included in the filing reflect thecorrection of an error to previously issued financial statements.☐ Indicate by check mark whether any of those error corrections are restatements that required a recovery analysis of incentive-based compensation received by any of theregistrant’s executive officers during the relevant recovery period pursuant to §240.10D-1(b).☐ Indicate by check mark which basis of accounting the registrant has used to prepare the financial statements included in this filing: International Financial Reporting Standards as issued by the International Accounting Standards Board☐Other☐ If this is an annual report, indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Act).Yes☐No☒ ASPEN INSURANCE HOLDINGS LIMITEDFORM20-FTABLE OF CONTENTS Explanatory Note PART I Item1.Identity of Directors, Senior Management and AdvisorsItem 2.Offer Statistics and Expected TimetableItem3.Key InformationItem 4.Information on the CompanyItem4A.Unresolved Staff CommentsItem5.Operating and Financial Review and ProspectsItem 6.Directors, Senior Management and EmployeesItem7.Major Shareholders and Related Party TransactionsItem 8.Financial InformationItem9.The Offer and ListingItem 10.Additional InformationItem11.Quantitative and Qualitative Disclosures about Market RiskItem 12.Description of Securities Other than Equity Securities PART II Item 13.Defaults, Dividend Arrearages and DelinquenciesItem 14.Material Modifications to the Rights of Security Holders and Use of ProceedsItem 15.Controls and ProceduresItem 16A.Audit Committee Financial ExpertItem 16B.Code of ConductItem 16C.Principal Accountant Fees and ServicesItem 16D.Exemptions from the Listing Standards for Audit CommitteesItem 16E.Purchases of Equity Securities by the Issuer and Affiliated PurchasersItem 16F.Change in Registrant’s Certifying AccountItem 16G.Corporate GovernanceItem 16H.Mine Safety DisclosureItem 16I.Disclosu