| League Two | 07/08/21 | Stranraer FC | - | Annan Athletic | 0:3 | ||||
| League Two | 06/11/21 | Annan Athletic | - | Stranraer FC | 2:2 | ||||
| League Two | 02/01/22 | Stranraer FC | - | Annan Athletic | 1:1 | ||||
| League Two | 05/03/22 | Annan Athletic | - | Stranraer FC | 4:1 | ||||
| League Two | 30/07/22 | Stranraer FC | - | Annan Athletic | 1:0 | ||||
| League Two | 26/11/22 | Stranraer FC | - | Annan Athletic | 1:1 | ||||
| League Two | 25/03/23 | Annan Athletic | - | Stranraer FC | 0:0 | ||||
| League One | 17/08/24 | Queen Of The South | - | Annan Athletic | 2:0 | ||||
| League One | 26/10/24 | Annan Athletic | - | Queen Of The South | 1:0 | ||||
| League One | 05/04/25 | Annan Athletic | - | Queen Of The South | 0:2 |
Scotland