Mr. Ryan Marr reports

CHESSWOOD GROUP LIMITED ANNOUNCES SEPTEMBER 2023 DIVIDEND

Chesswood Group Ltd. today declared a dividend in an amount of one cent per share for the month of September, payable on Oct. 16, 2023, to shareholders of record at the close of business on Sept. 29, 2023.

Chesswood advises that the dividend declared for the month ending Sept. 30, 2023, will be an eligible dividend for the purposes of the Income Tax Act (Canada) and any similar provincial legislation.

As noted in the company's news release announcing the dividend for August, the actions by central banks to significantly raise interest rates has affected the business climate generally and has temporarily compressed the company's net interest margins. As contemplated in that news release, management and the company's directors conducted a thorough evaluation of its portfolio performance and various interest rate scenarios on its profitability and concluded that a temporary adjustment to its dividend rate was warranted in order to pro-actively address this period of macroeconomic uncertainty. "This temporary measure will allow us to conserve capital and focus on various growth opportunities in the near term that will ultimately enhance long-term shareholder value," said Ryan Marr, Chesswood's president and chief executive officer.

About Chesswood Group Ltd.

Chesswood Group is a Toronto, Canada-based, holding company 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).