| League Two | 15.04.23 | Annan Athletic | - | Albion Rovers | 4:0 | ||||
| League Cup | 18.07.23 | Dunfermline Athletic | - | Annan Athletic | 4:0 | ||||
| League One | 07.10.23 | Cove Rangers | - | Annan Athletic | 3:2 | ||||
| League One | 17.02.24 | Annan Athletic | - | Stirling Albion FC | 2:1 | ||||
| League One | 30.03.24 | Alloa Athletic | - | Annan Athletic | 1:1 | ||||
| League One | 05.10.24 | Annan Athletic | - | Montrose FC | 1:0 | ||||
| League One | 16.11.24 | Annan Athletic | - | Kelty Hearts | 0:2 | ||||
| League One | 19.04.25 | Annan Athletic | - | Arbroath FC | 5:1 |
Schotland