| League Two | 25.09.21 | Annan Athletic | - | Edinburgh City FC | 1:3 |  |
|||
| League Two | 03.12.21 | Edinburgh City FC | - | Annan Athletic | 0:1 | ||||
| League Two | 05.03.22 | Annan Athletic | - | Stranraer FC | 4:1 |  |
|||
| League Two | 30.07.22 | Stranraer FC | - | Annan Athletic | 1:0 | ||||
| League Two | 15.10.22 | Annan Athletic | - | Stranraer FC | 1:1 | |
|||
| League Two | 25.03.23 | Annan Athletic | - | Stranraer FC | 0:0 | ||||
| FA Cup | 25.11.23 | Annan Athletic | - | Dumbarton FC | 4:5 n.v. | |
|||
| League One | 14.09.24 | Annan Athletic | - | Dumbarton FC | 1:1 | |
|||
| League One | 08.02.25 | Annan Athletic | - | Dumbarton FC | 2:1 | ||||
| League One | 26.04.25 | Dumbarton FC | - | Annan Athletic | 3:1 | |
Schotland