| League Cup | 10.11.20 | Albion Rovers | - | Annan Athletic | 1:5 |  |
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| League Two | 02.04.22 | Stenhousemuir FC | - | Annan Athletic | 0:1 | ||||
| League Two | 27.08.22 | Albion Rovers | - | Annan Athletic | 2:2 | |
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| League One | 11.11.23 | Montrose FC | - | Annan Athletic | 1:1 | |
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| League One | 16.12.23 | Stirling Albion FC | - | Annan Athletic | 1:1 | |
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| League Cup | 17.08.24 | The Spartans FC | - | Ross County FC | 1:0 |
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