| League Two | 28.01.23 | Annan Athletic | - | East Fife FC | 3:0 | ||||
| League One | 12.08.23 | Annan Athletic | - | Montrose FC | 1:3 | ||||
| League One | 06.01.24 | Annan Athletic | - | Montrose FC | 2:2 | ||||
| League One | 23.11.24 | Montrose FC | - | Annan Athletic | 2:1 | ||||
| League One | 25.01.25 | Annan Athletic | - | Montrose FC | 2:2 |
Écosse