| League Two | 16.10.21 | Forfar Athletic | - | Annan Athletic | 2:0 | ||||
| League Cup | 16.07.22 | Annan Athletic | - | Elgin City | 4:0 | ||||
| League Two | 20.08.22 | Annan Athletic | - | Stirling Albion FC | 1:2 |  |
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| League Two | 07.01.23 | Annan Athletic | - | Forfar Athletic | 0:2 | ||||
| Playoffs | 13.05.23 | Dumbarton FC | - | Annan Athletic | 0:0 | ||||
| League Two | 05.08.23 | Bonnyrigg Rose Athletic | - | Dumbarton FC | 1:1 | ||||
| League One | 05.04.25 | Kelty Hearts | - | Dumbarton FC | 0:6 | ||||
| League One | 19.04.25 | Montrose FC | - | Dumbarton FC | 2:2 |  |
Schottland