| League Two | 07/08/21 | Stranraer FC | - | Annan Athletic | 0:3 |  |
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| League Two | 25/09/21 | Annan Athletic | - | Edinburgh City FC | 1:3 | ||||
| League Two | 20/11/21 | Annan Athletic | - | Albion Rovers | 1:1 | ||||
| League Two | 08/01/22 | Cowdenbeath FC | - | Annan Athletic | 1:3 | ||||
| League Two | 22/04/22 | Edinburgh City FC | - | Annan Athletic | 2:1 | ||||
| Playoffs | 03/05/22 | Annan Athletic | - | Forfar Athletic | 1:0 | ||||
| League Two | 18/02/23 | Stenhousemuir FC | - | Albion Rovers | 2:0 | ||||
| League Two | 15/04/23 | Annan Athletic | - | Albion Rovers | 4:0 | ||||
| League One | 05/10/24 | Annan Athletic | - | Montrose FC | 1:0 | ||||
| League One | 16/11/24 | Annan Athletic | - | Kelty Hearts | 0:2 |
Scotland