| League Two | 21/08/21 | Albion Rovers | - | Annan Athletic | 0:1 | ||||
| League Two | 02/03/22 | Albion Rovers | - | Annan Athletic | 1:4 | ||||
| League Two | 13/08/22 | Dumbarton FC | - | Annan Athletic | 4:0 |  |
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| League Two | 11/02/23 | Dumbarton FC | - | Annan Athletic | 2:1 | ||||
| League Two | 08/04/23 | Annan Athletic | - | Dumbarton FC | 3:1 | ||||
| Playoffs | 09/05/23 | Annan Athletic | - | Dumbarton FC | 6:0 | ||||
| Playoffs | 13/05/23 | Dumbarton FC | - | Annan Athletic | 0:0 |
Scotland