Mr. Ryan Marr reports

CHESSWOOD GROUP LIMITED ANNOUNCES OCTOBER 2023 DIVIDEND

Chesswood Group Ltd. has declared a dividend in an amount of one cent per share for the month of October, payable on Nov. 15, 2023, to shareholders of record at the close of business on Oct. 31, 2023.

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

About Chesswood Group Ltd.

Based in Toronto, Canada, Chesswood Group is a 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).