| League Two | 04.03.23 | Annan Athletic | - | Stenhousemuir FC | 2:3 | ||||
| League One | 19.08.23 | Queen Of The South | - | Annan Athletic | 3:1 |  |
|||
| League One | 21.10.23 | Annan Athletic | - | Queen Of The South | 0:1 | |
|||
| League One | 30.12.23 | Queen Of The South | - | Annan Athletic | 2:1 | |
 |
||
| League One | 09.03.24 | Annan Athletic | - | Queen Of The South | 2:1 | |
|||
| League One | 21.09.24 | Arbroath FC | - | Annan Athletic | 2:0 | |
|||
| League One | 21.12.24 | Annan Athletic | - | Arbroath FC | 0:4 | |
Schottland