Mr. Ryan Marr reports

CHESSWOOD PROVIDES UPDATE ON STRATEGIC REVIEW PROCESS

Chesswood Group Ltd. has provided an update on its review of strategic alternatives to maximize shareholder value, previously announced on Jan. 22, 2024.

In connection with the review process, Chesswood, through a special committee of its board of directors comprising Edward Sonshine (chair), Catherine Barbaro and Rags Davloor, has engaged Stikeman Elliott LLP as legal counsel and RBC Capital Markets as its exclusive financial adviser to assist with the special committee's evaluation of potential strategic alternatives to determine the best path forward to maximizing value for shareholders.

As a result of the meaningful level of inbound interest from potential counterparties, the special committee intends to continue its efforts in exploring all available strategic initiatives. While the intention is to complete the review process in a timely manner, there can be no assurances as to the timing for completion of review by the special committee or that this process will result in any particular outcome. As such, undue reliance should not be placed on any expectations as to potential transactions or strategic alternatives that may be or may become available to Chesswood, or that there be any impact on shareholder value following completion of such review. Except as may be required by applicable securities laws, Chesswood does not expect to comment further regarding the special committee's review process until it determines additional disclosure is necessary or advisable.

About Chesswood Group Ltd.

Chesswood Group is a Toronto, Canada, based holding company the subsidiaries of which engage in the business of specialty finance (including equipment finance throughout North America, and vehicle finance and legal sector finance in Canada), as well as the origination and management of private credit alternatives for North American investors. The company's shares trade on the Toronto Stock Exchange (under the symbol CHW).