| League Two | 21.08.21 | Albion Rovers | - | Annan Athletic | 0:1 | ||||
| League Two | 30.10.21 | Annan Athletic | - | Cowdenbeath FC | 1:0 | ||||
| FA Cup | 27.11.21 | Gala Fairydean Rovers | - | Annan Athletic | 0:1 | ||||
| League Two | 01.04.23 | Forfar Athletic | - | Albion Rovers | 2:1 | ||||
| League Two | 23.12.23 | The Spartans FC | - | Stranraer FC | 3:0 | ||||
| League Two | 05.03.24 | Stranraer FC | - | Dumbarton FC | 5:0 | ||||
| League Two | 23.03.24 | East Fife FC | - | Stranraer FC | 2:1 | ||||
| League One | 28.09.24 | Kelty Hearts | - | Annan Athletic | 3:0 |
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