| League Two | 21.08.21 | Albion Rovers | - | Annan Athletic | 0:1 | ||||
| FA Cup | 27.11.21 | Gala Fairydean Rovers | - | Annan Athletic | 0:1 | ||||
| League Two | 03.09.22 | Annan Athletic | - | Forfar Athletic | 2:1 |  |
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| League One | 02.09.23 | Kelty Hearts | - | Annan Athletic | 1:1 | ||||
| League One | 28.09.24 | Kelty Hearts | - | Annan Athletic | 3:0 |
Inglaterra