| 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 |  |
Scotland