| 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 |
England