| 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 |
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