| League Cup | 10.07.21 | Airdrieonians FC | - | Annan Athletic | 4:5 i.E. | ||||
| 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 Two | 06.08.22 | Albion Rovers | - | Dumbarton FC | 1:2 |  |
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| League Two | 29.04.23 | East Fife FC | - | Albion Rovers | 2:1 | ||||
| League Two | 13.01.24 | Stranraer FC | - | Peterhead FC | 2:0 | ||||
| League Two | 20.04.24 | Stranraer FC | - | Dumbarton FC | 0:0 |
Schottland