| League Two | 03.12.22 | East Fife FC | - | Annan Athletic | 1:3 |  |
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| League Two | 25.03.23 | Annan Athletic | - | Stranraer FC | 0:0 |  |
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| League Two | 06.05.23 | Stenhousemuir FC | - | Annan Athletic | 2:1 | |
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| League One | 03.02.24 | Annan Athletic | - | Alloa Athletic | 2:3 | ||||
| League One | 16.03.24 | Montrose FC | - | Annan Athletic | 1:1 |
Inglaterra