| League One | 15.04.23 | Dunfermline Athletic | - | Queen Of The South | 5:0 | ||||
| League One | 16.09.23 | Annan Athletic | - | Stirling Albion FC | 3:0 | ||||
| League One | 04.11.23 | Annan Athletic | - | Kelty Hearts | 2:2 | ||||
| League One | 09.12.23 | Annan Athletic | - | Cove Rangers | 1:3 | ||||
| League One | 20.04.24 | Edinburgh City | - | Annan Athletic | 1:2 | ||||
| Playoffs | 13.05.25 | East Fife FC | - | Annan Athletic | 3:2 |
Escocia