| League Cup | 10.10.20 | Annan Athletic | - | Stranraer FC | 4:5 d.p. | ||||
| League Two | 06.11.21 | Annan Athletic | - | Stranraer FC | 2:2 | ||||
| League Two | 02.01.22 | Stranraer FC | - | Annan Athletic | 1:1 | ||||
| League Two | 27.08.22 | Albion Rovers | - | Annan Athletic | 2:2 |  |
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| League Two | 23.12.22 | Annan Athletic | - | Albion Rovers | 5:1 | ||||
| League Two | 25.02.23 | Albion Rovers | - | Annan Athletic | 0:2 |
Schotland