CHESSWOOD RENEWS NORMAL COURSE ISSUER BID AND INITIATES AUTOMATIC SHARE PURCHASE PLAN

TORONTO, AUGUST 23, 2016 – Chesswood Group Limited (“Chesswood”) (TSX: CHW)
announced today that the Toronto Stock Exchange (the “TSX”) has accepted its notice of intention
to conduct a normal course issuer bid to enable it to purchase up to 1,078,096 of its 16,389,554
Common Shares (“Shares”) outstanding, representing approximately 10 per cent of Chesswood’s
public float of 10,780,962 Shares as of August 22, 2016. The average daily trading volume of
Chesswood for the past six months was 14,150, and a maximum of 3,537 Shares (being
approximately 25% of the average daily trading volume during the preceding six months) may be
purchased by Chesswood on any one day under its normal course issuer bid, except where
purchases are made in accordance with “block purchases” exemptions under applicable TSX
policies.

The normal course issuer bid will commence on August 25, 2016, and will terminate on the earlier
of August 24, 2017, the date Chesswood completes its purchases pursuant to the notice of intention
to make a normal course issuer bid filed with the TSX or the date of notice by Chesswood of
termination of the bid.

Chesswood has purchased 18,085 of its outstanding Shares at an weighted average price of
$10.53 per Share in connection with its previous normal course issuer bid, which expires on August
24, 2016. Chesswood believes that the market price of the Shares at certain times may be
attractive and that the purchase of Shares from time to time would be an appropriate use of its
funds in light of potential benefits to remaining shareholders.

Chesswood also announces that it will enter into an automatic share purchase plan agreement
(“ASPP”) with a broker to allow for the purchase of its Shares under the NCIB at times when
Chesswood normally would not be active in the market due to regulatory restrictions or self-imposed
trading blackout periods. Before entering into a blackout period, Chesswood may, but is not
required to, instruct the designated broker to make purchases under the NCIB in accordance with
the terms of the ASPP. Such purchases will be determined by the broker in its sole discretion based
on parameters established by Chesswood prior to the blackout period in accordance with TSX rules
and the terms of the ASPP. The terms of the ASPP have been pre-cleared by the TSX. Outside of
these pre-determined blackout periods, Shares will be purchased in accordance with Management’s
discretion.

Chesswood will make purchases on the open market through the facilities of the TSX in accordance
with the rules and policies of the TSX. The price that Chesswood will pay for any such Shares will
be the market price of such Shares on the TSX at the time of acquisition. Shares purchased under
the bid will be cancelled following purchase.

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.BlueChipLeasing.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.

You might also like

• Chesswood Announces Second Quarter Results for 2016
  August 12, 2016