X0306 5 2019-08-31 0 1 0001099369 DESTINY MEDIA TECHNOLOGIES INC DSNY 0001655366 Boenisch Sandra #1110 - 885 WEST GEORGIA STREET VANCOUVER A1 V6C 3E8 BRITISH COLUMBIA, CANADA 0 1 0 0 Chief Financial Officer COMMON 2019-08-31 4 A 0 5643 1.25 A 15984 D STOCK OPTION (RIGHT TO BUY) 1.05 2019-06-25 5 A 0 10000 0 A 2022-12-13 COMMON 10000 10000 D STOCK OPTION (RIGHT TO BUY) 1.75 2019-06-25 5 A 0 20000 0 A 2022-12-13 COMMON 20000 20000 D STOCK OPTION (RIGHT TO BUY) 2.00 2019-06-25 5 D 0 30000 0 D 2022-12-13 COMMON 30000 0 D Purchased under Employee Stock Purchase Plan, which transactions are exempt under Rule 16b-3(c) of the Securities Exchange Act of 1934. The price reported in Column 4 is a weighted average price. These shares were purchased in multiple transactions at prices ranging from $0.98 to $1.50, inclusive. The reporting person undertakes to provide to Destiny Media Technologies Inc., any security holder of Destiny Media Technologies Inc. or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price within the ranges set forth in this footnote. The weighted average price reported above was converted from the Canadian weighted average price of C$1.66 to USD using an exchange rate of CAD $1.3294=USD $1.00. Reflects 5:1 stock consolidation effected by Destiny Media Technologies Inc. on September 13, 2019. The reporting person agreed to cancellation of an option granted on December 13, 2017 exchange for new options having a lower exercise price. The options are vesting in equal monthly installments over a two-year period which commenced on December 31, 2017. /s/ Sandra Boenisch 2019-10-03