| League Two | 07/08/21 | Stranraer FC | - | Annan Athletic | 0:3 | ||||
| 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 |  |
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| League Two | 22/04/22 | Edinburgh City FC | - | Annan Athletic | 2:1 | ||||
| Playoffs | 03/05/22 | Annan Athletic | - | Forfar Athletic | 1:0 | ||||
| League Cup | 19/07/22 | Annan Athletic | - | Ayr United | 5:4 pso | |
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| League Two | 29/10/22 | Annan Athletic | - | Dumbarton FC | 0:1 | ||||
| League Two | 21/01/23 | Annan Athletic | - | Bonnyrigg Rose Athletic | 4:0 | ||||
| League Two | 15/04/23 | Annan Athletic | - | Albion Rovers | 4:0 | ||||
| League Two | 13/01/24 | Bonnyrigg Rose Athletic | - | Dumbarton FC | 1:1 | ||||
| Playoffs | 11/05/24 | Stirling Albion FC | - | Dumbarton FC | 0:0 |  |
Scotland