| 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 aet | |
|||
| 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 | |
Scotland