| 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 pn. | |
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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 |  |
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