| League Cup | 25/07/17 | Dumbarton FC | - | Annan Athletic | 3:4 pso | ||||
| 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 aet | ||||
| League One | 14/12/24 | Dumbarton FC | - | Annan Athletic | 1:5 | ||||
| League One | 26/04/25 | Dumbarton FC | - | Annan Athletic | 3:1 |
Scotland