Hamilton Insurance Group, Ltd.

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, D.C. 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of

the Securities Exchange Act of 1934

Filed by the Registrant ☒

Filed by a Party other than the Registrant ☐

Check the appropriate box:

HAMILTON INSURANCE GROUP, LTD.

(Name of Registrant as Specified In Its Charter)

(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

Payment of Filing Fee (Check the appropriate box):

Notice of 2026 Annual General

Meeting of Shareholders

On behalf of the Hamilton Insurance Group, Ltd. Board of Directors,(the "Board of Directors" or "Board") you are cordially invited to attend the Hamilton 2026 Annual General Meeting of Shareholders (the “Annual Meeting" or “Annual General Meeting”).

Meeting Details

How To Vote

Matters to Be Voted On

We may also transact any other business as may properly come before the meeting. As of the date of this proxy statement, we are not aware of any business to be presented for consideration other than the matters described above.

Proxies

The Board of Directors is soliciting proxies to be voted at the Annual Meeting on May 5, 2026, and at any postponed or reconvened meeting. Shareholders of record are being mailed, sent or given, on or about March 24, 2026, a Notice of Internet Availability of Proxy Materials providing instructions on how to access the Proxy Materials on the Internet.

Accessing the 2026 Annual General Meeting

Your vote is important—we value input from all of our shareholders.

Please take time to review the accompanying proxy statement, which includes important details about the proposals to be considered at the Annual General Meeting.

To join the meeting and vote, you will need the 16-digit control number found on your Notice of Internet Availability of Proxy Materials, your proxy card, or any voting instruction form included with these materials.

This year’s Annual General Meeting will be held in a virtual format, allowing shareholders to attend, vote, and submit questions online. We believe this approach enhances accessibility and encourages meaningful engagement with management, no matter where you are located. You are encouraged to participate virtually and vote your shares in advance by proxy.

For more information on voting and participating in the virtual meeting, please refer to the “Voting and Meeting Information” section in the proxy statement.

By order of the Board,

Gemma Carreiro

General Counsel & Secretary

March 24, 2026

Important Notice Regarding the Availability of Proxy Materials to be held virtually via the Internet on May 5, 2026. Our 2026 proxy statement as well as our 2025 Annual Report are available free of charge in the investors section of our website at www.hamiltongroup.com.

Table of Contents

Cautionary Note Regarding Forward-Looking Statements

This proxy statement contains forward-looking statements within the meaning of the U.S. Private Securities Litigation Reform Act of 1995. Forward-looking statements can be identified by the use of terms such as “believes,” “expects,” “may,” “will,” “target,” “should,” “could,” “would,” “seeks,” “intends,” “plans,” “contemplates,” “estimates,” or “anticipates,” or similar expressions which concern our strategy, plans, projections or intentions. These forward-looking statements appear throughout this proxy statement and address such matters such as our industry, growth strategy, market position, future operations, margins, profitability, capital expenditures, liquidity and capital resources, corporate governance practices, risk management, shareholder engagement, executive and director compensation programs, and equity compensation utilization. By their nature, forward-looking statements: speak only as of the date they are made; are not statements of historical fact or guarantees of future performance; and are subject to risks, uncertainties, assumptions, and changes in circumstances that are difficult to predict or quantify. Although we believe our expectations and projections are reasonable, actual results may differ materially.

Factors that can cause results to differ materially include those described under “Special Note Regarding Forward-Looking Statements” in Hamilton's Annual Report on Form 10-K ("Annual Report") filed with the Securities and Exchange Commission ("SEC") and available on our website, as well as other risks and uncertainties. You should evaluate all forward-looking statements in the context of these risks and uncertainties.

We cannot assure you that we will achieve the results or developments we expect or, even if realized, that they will have the anticipated effects. All forward-looking statements in this proxy statement apply only as of its date and are expressly qualified in their entirety by this cautionary note. We undertake no obligation to publicly update or revise any forward-looking statements to reflect subsequent events or circumstances.

When used in this proxy statement, unless otherwise mentioned or unless the context indicates otherwise, the terms "we", "us", "our", the "Company", the "Group" and "Hamilton" refer to Hamilton Insurance Group, Ltd. and its consolidated subsidiaries.