CHESSWOOD ANNOUNCES SALE OF CASE FUNDING OPERATIONS

Sale is part of strategic alignment and capital deployment maximization TORONTO, February 4, 2015. Chesswood Group Limited (“Chesswood”) (TSX: CHW) is pleased to announce that it has successfully completed the sale of the operations of its Case
Funding subsidiary along with most of Case Funding’s attorney loan portfolio, to a U.S. based private equity firm.

The purchase price paid to Case Funding was US$4.4 million. The sale, which results in a small pre-tax net gain, will allow both capital and Chesswood management attention to be focused on the expansion of Chesswood’s other North American businesses. “While the offer to purchase the Case Funding operations was unsolicited, we saw the transaction as not only providing us with a modest gain on our investment of only a few years, but more importantly an opportunity to seek both organic growth and acquisitions that are better aligned with our desire to invest in scalable finance businesses” said Barry Shafran, Chesswood’s President and CEO. “This sale and our recently entered into credit facility are two more steps toward our strategic growth and capital allocation initiatives. In addition to the attorney portfolio, the purchaser takes over the very capable Case Funding team and operations, which did an outstanding job of taking a start-up business to profitability in a very short time”.

Most of Chesswood’s earnings are generated in U.S. dollars by our American subsidiaries Pawnee Leasing Corporation and Windset Capital Corporation. Chesswood’s strategic focus is the growth, both organically and through acquisitions, of its North American finance businesses, composed of companies that can provide superior returns on capital.

About Chesswood Group Limited – Chesswood Group Limited is a financial services company with operating businesses in both Canada and the U.S.

To learn more about Chesswood Group Limited, visit www.ChesswoodGroup.com .

The separate websites of Chesswood Group Limited’s operating businesses are at

www.PawneeLeasing.com , www.WindsetCapital.com , www.nstarleasing.com and www.AcuraSherway.com.

Contact:
Barry Shafran
Chesswood Group Limited
416-386-3099
bshafran@chesswoodgroup.com

This press release contains forward-looking statements that involve a number of risks and uncertainties because they relate to events and depend on circumstances that will occur in the future. Many factors could cause actual results and developments to differ materially from those expressed or implied by these forward-looking statements. NO STOCK EXCHANGE, SECURITIES COMMISSION OR OTHER REGULATORY AUTHORITY HAS APPROVED OR DISAPPROVED THE INFORMATION CONTAINED HEREIN.