| League Two | 08.10.22 | Stenhousemuir FC | - | Annan Athletic | 2:2 | ||||
| League Two | 18.02.23 | Annan Athletic | - | Stirling Albion FC | 2:2 | ||||
| League Two | 08.04.23 | Annan Athletic | - | Dumbarton FC | 3:1 | ||||
| League One | 06.01.24 | Annan Athletic | - | Montrose FC | 2:2 | ||||
| League One | 26.10.24 | Annan Athletic | - | Queen Of The South | 1:0 | ||||
| League One | 11.01.25 | Alloa Athletic | - | Queen Of The South | 1:1 |  |
Guadeloupe