| League Cup | 10/07/21 | Airdrieonians FC | - | Annan Athletic | 4:5 pso | ||||
| League Two | 15/01/22 | Annan Athletic | - | Forfar Athletic | 2:2 | ||||
| League Two | 26/03/22 | Annan Athletic | - | Albion Rovers | 2:4 | ||||
| Playoffs | 07/05/22 | Forfar Athletic | - | Annan Athletic | 1:1 | ||||
| League One | 28/10/23 | Edinburgh City | - | Annan Athletic | 3:2 | ||||
| League One | 23/12/23 | Annan Athletic | - | Falkirk FC | 0:3 | ||||
| League One | 10/02/24 | Hamilton Academical | - | Annan Athletic | 2:3 | ||||
| League One | 02/03/24 | Falkirk FC | - | Annan Athletic | 1:1 | ||||
| League One | 21/09/24 | Stenhousemuir FC | - | Queen Of The South | 0:0 | ||||
| League One | 05/10/24 | Queen Of The South | - | Kelty Hearts | 1:5 |  |
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| League One | 16/11/24 | Dumbarton FC | - | Queen Of The South | 2:1 |  |
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| League One | 08/02/25 | Stenhousemuir FC | - | Queen Of The South | 2:1 | ||||
| League One | 12/04/25 | Queen Of The South | - | Montrose FC | 2:1 | |
England