| 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 | ||||
| League Two | 03/05/25 | East Fife FC | - | Elgin City | 2:0 |
Scotland