| FA Cup | 23.03.21 | Formartine United | - | Annan Athletic | 3:1 pn. |  |
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| League Two | 14.08.21 | Annan Athletic | - | Stirling Albion FC | 3:1 | ||||
| Playoffs | 09.05.23 | Annan Athletic | - | Dumbarton FC | 6:0 | |
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| League One | 21.10.23 | Annan Athletic | - | Queen Of The South | 0:1 | ||||
| League One | 13.01.24 | Kelty Hearts | - | Annan Athletic | 1:1 | |
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