| League Cup | 25.07.17 | Dumbarton FC | - | Annan Athletic | 3:4 pn. | ||||
| League Two | 21.08.21 | Albion Rovers | - | Annan Athletic | 0:1 | ||||
| League Two | 20.11.21 | Annan Athletic | - | Albion Rovers | 1:1 | ||||
| League Two | 02.03.22 | Albion Rovers | - | Annan Athletic | 1:4 |  |
 |
||
| League Two | 26.03.22 | Annan Athletic | - | Albion Rovers | 2:4 | ||||
| League Two | 13.08.22 | Dumbarton FC | - | Annan Athletic | 4:0 | ||||
| League Two | 29.10.22 | Annan Athletic | - | Dumbarton FC | 0:1 | ||||
| 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 | ||||
| FA Cup | 25.11.23 | Annan Athletic | - | Dumbarton FC | 4:5 pró. | ||||
| League One | 14.12.24 | Dumbarton FC | - | Annan Athletic | 1:5 |
Escocia