| League Two | 03.09.22 | Annan Athletic | - | Forfar Athletic | 2:1 | ||||
| League One | 12.08.23 | Annan Athletic | - | Montrose FC | 1:3 | ||||
| League One | 02.09.23 | Kelty Hearts | - | Annan Athletic | 1:1 | ||||
| League One | 27.04.24 | Queen Of The South | - | Cove Rangers | 2:0 | ||||
| League One | 28.09.24 | Kelty Hearts | - | Annan Athletic | 3:0 |
Inglaterra