| 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 One | 24.08.24 | Kelty Hearts | - | Inverness CT | 0:0 | ||||
| League One | 28.09.24 | Kelty Hearts | - | Annan Athletic | 3:0 | ||||
| League One | 26.10.24 | Stenhousemuir FC | - | Kelty Hearts | 2:1 | ||||
| FA Cup | 30.11.24 | Elgin City | - | Kelty Hearts | 3:2 |
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