| League Two | 21/08/21 | Albion Rovers | - | Annan Athletic | 0:1 | ||||
| League Two | 30/10/21 | Annan Athletic | - | Cowdenbeath FC | 1:0 | ||||
| FA Cup | 27/11/21 | Gala Fairydean Rovers | - | Annan Athletic | 0:1 | ||||
| League Two | 03/09/22 | Annan Athletic | - | Forfar Athletic | 2:1 | ||||
| League One | 12/08/23 | Annan Athletic | - | Montrose FC | 1:3 | ||||
| League One | 02/09/23 | Kelty Hearts | - | Annan Athletic | 1:1 | ||||
| League One | 28/09/24 | Kelty Hearts | - | Annan Athletic | 3:0 |
Scotland