| League Cup | 02.08.14 | Dunfermline Athletic | - | Annan Athletic | 5:1 | ||||
| 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 |
Schotland