Mr. Ryan Marr reports

CHESSWOOD GROUP LIMITED ANNOUNCES MAY 2023 DIVIDEND

Chesswood Group Ltd. has declared a dividend in an amount of five cents per share for the month of May, payable on June 15, 2023, to shareholders of record at the close of business on May 31, 2023.

Chesswood Group advises that, unless indicated otherwise, the dividend declared for the month ending May 31, 2023, and all future dividends will be eligible dividends for the purposes of the Income Tax Act (Canada) and any similar provincial legislation.

About Chesswood Group Ltd.

Chesswood Group is a holding company based in Toronto, Canada, whose subsidiaries 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).