| League Two | 11.09.21 | Kelty Hearts | - | Elgin City | 1:1 | ||||
| League Two | 18.12.21 | Stranraer FC | - | Kelty Hearts | 0:4 | ||||
| Playoffs | 03.05.22 | Annan Athletic | - | Forfar Athletic | 1:0 | ||||
| League Cup | 19.07.22 | Annan Athletic | - | Ayr United | 5:4 i.E. | ||||
| 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 |  |
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| League Cup | 18.07.23 | Dunfermline Athletic | - | Annan Athletic | 4:0 | |
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| League One | 07.10.23 | Cove Rangers | - | Annan Athletic | 3:2 | ||||
| League One | 16.11.24 | Annan Athletic | - | Kelty Hearts | 0:2 | ||||
| League One | 19.04.25 | Annan Athletic | - | Arbroath FC | 5:1 |
Schottland