| League Two | 30.10.21 | Kelty Hearts | - | Stirling Albion FC | 1:1 | ||||
| League Two | 26.02.22 | Kelty Hearts | - | Annan Athletic | 3:1 | ||||
| League Two | 30.07.22 | Stranraer FC | - | Annan Athletic | 1:0 | ||||
| League Two | 05.11.22 | Forfar Athletic | - | Annan Athletic | 1:4 | ||||
| League Two | 11.03.23 | Annan Athletic | - | Elgin City | 4:1 | ||||
| League One | 16.09.23 | Annan Athletic | - | Stirling Albion FC | 3:0 | ||||
| Playoffs | 13.05.25 | East Fife FC | - | Annan Athletic | 3:2 |  |
 |
Schottland