| League Two | 28.08.21 | Cowdenbeath FC | - | Annan Athletic | 1:3 | ||||
| League Two | 30.10.21 | Annan Athletic | - | Cowdenbeath FC | 1:0 | ||||
| League Two | 09.04.22 | Annan Athletic | - | Cowdenbeath FC | 2:3 | ||||
| League One | 12.08.23 | Annan Athletic | - | Montrose FC | 1:3 | ||||
| League One | 11.11.23 | Montrose FC | - | Annan Athletic | 1:1 | ||||
| League One | 06.01.24 | Annan Athletic | - | Montrose FC | 2:2 | ||||
| League One | 16.03.24 | Montrose FC | - | Annan Athletic | 1:1 | ||||
| League One | 05.10.24 | Annan Athletic | - | Montrose FC | 1:0 | ||||
| League One | 23.11.24 | Montrose FC | - | Annan Athletic | 2:1 | ||||
| League One | 25.01.25 | Annan Athletic | - | Montrose FC | 2:2 | ||||
| League One | 22.03.25 | Montrose FC | - | Annan Athletic | 3:1 |
Schottland