| FA Cup | 29.11.14 | Annan Athletic | - | Brechin City FC | 1:1 | ||||
| FA Cup | 09.12.14 | Brechin City FC | - | Annan Athletic | 4:2 | ||||
| League Two | 20.08.22 | Annan Athletic | - | Stirling Albion FC | 1:2 | ||||
| League Two | 12.11.22 | Stirling Albion FC | - | Annan Athletic | 0:2 | ||||
| League Two | 18.02.23 | Annan Athletic | - | Stirling Albion FC | 2:2 | ||||
| League Two | 22.04.23 | Stirling Albion FC | - | Annan Athletic | 3:1 | ||||
| League One | 16.12.23 | Stirling Albion FC | - | Annan Athletic | 1:1 | ||||
| League One | 17.02.24 | Annan Athletic | - | Stirling Albion FC | 2:1 | ||||
| League One | 04.05.24 | Stirling Albion FC | - | Annan Athletic | 1:1 |  |
Schotland