| 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 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 |
Escocia