| League Two | 18.12.21 | Stranraer FC | - | Kelty Hearts | 0:4 |  |
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| League Two | 26.02.22 | Stranraer FC | - | Albion Rovers | 0:0 | ||||
| League Two | 26.03.22 | Stirling Albion FC | - | Stranraer FC | 1:0 | ||||
| League Cup | 19.07.22 | Annan Athletic | - | Ayr United | 5:4 pn. | ||||
| League Two | 29.10.22 | Annan Athletic | - | Dumbarton FC | 0:1 | |
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| League Two | 21.01.23 | Annan Athletic | - | Bonnyrigg Rose Athletic | 4:0 | ||||
| League Two | 15.04.23 | Annan Athletic | - | Albion Rovers | 4:0 | ||||
| League One | 07.10.23 | Cove Rangers | - | Annan Athletic | 3:2 | |
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| League One | 17.02.24 | Annan Athletic | - | Stirling Albion FC | 2:1 | ||||
| League One | 30.03.24 | Alloa Athletic | - | Annan Athletic | 1:1 |  |
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| League One | 16.11.24 | Annan Athletic | - | Kelty Hearts | 0:2 | ||||
| League One | 19.04.25 | Annan Athletic | - | Arbroath FC | 5:1 | |
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Escocia