| League Two | 03.12.21 | Edinburgh City FC | - | Annan Athletic | 0:1 | ||||
| League Cup | 09.07.22 | Queen Of The South | - | Annan Athletic | 2:3 | ||||
| League One | 03.02.24 | Annan Athletic | - | Alloa Athletic | 2:3 |  |
|||
| League One | 13.02.24 | Alloa Athletic | - | Annan Athletic | 2:1 | ||||
| League One | 24.08.24 | Annan Athletic | - | Alloa Athletic | 0:1 | ||||
| League One | 02.11.24 | Alloa Athletic | - | Annan Athletic | 5:0 | ||||
| League One | 12.04.25 | Alloa Athletic | - | Annan Athletic | 1:0 |
Escocia