| League Two | 02.10.21 | Kelty Hearts | - | Annan Athletic | 2:1 | ||||
| League Two | 26.02.22 | Kelty Hearts | - | Annan Athletic | 3:1 | ||||
| League Two | 30.04.22 | Annan Athletic | - | Kelty Hearts | 1:2 | ||||
| League One | 31.08.24 | Stenhousemuir FC | - | Annan Athletic | 5:1 | ||||
| League One | 09.11.24 | Annan Athletic | - | Stenhousemuir FC | 1:1 | ||||
| League One | 04.01.25 | Stenhousemuir FC | - | Annan Athletic | 1:1 | ||||
| League One | 08.03.25 | Annan Athletic | - | Stenhousemuir FC | 0:2 |
Écosse