| League Two | 07.08.21 | Stranraer FC | - | Annan Athletic | 0:3 | ||||
| League Two | 25.09.21 | Annan Athletic | - | Edinburgh City FC | 1:3 |  |
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| League Two | 20.11.21 | Annan Athletic | - | Albion Rovers | 1:1 |  |
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| League Two | 08.01.22 | Cowdenbeath FC | - | Annan Athletic | 1:3 | ||||
| League Cup | 18.07.23 | Dunfermline Athletic | - | Annan Athletic | 4:0 | |
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| League One | 07.10.23 | Cove Rangers | - | Annan Athletic | 3:2 | ||||
| League One | 17.02.24 | Annan Athletic | - | Stirling Albion FC | 2:1 |  |
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| League One | 30.03.24 | Alloa Athletic | - | Annan Athletic | 1:1 | ||||
| League One | 25.01.25 | Queen Of The South | - | Dumbarton FC | 3:1 |
Angleterre