| League Two | 07/08/21 | Stranraer FC | - | Annan Athletic | 0:3 | ||||
| League Two | 02/01/22 | Stranraer FC | - | Annan Athletic | 1:1 |  |
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| League Two | 30/07/22 | Stranraer FC | - | Annan Athletic | 1:0 | |
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| League Two | 15/10/22 | Annan Athletic | - | Stranraer FC | 1:1 | ||||
| League Two | 26/11/22 | Stranraer FC | - | Annan Athletic | 1:1 | ||||
| League Two | 25/03/23 | Annan Athletic | - | Stranraer FC | 0:0 | |
England