| League Cup | 10.11.20 | Albion Rovers | - | Annan Athletic | 1:5 | ||||
| League Two | 02.04.22 | Stenhousemuir FC | - | Annan Athletic | 0:1 | ||||
| League One | 11.11.23 | Montrose FC | - | Annan Athletic | 1:1 | ||||
| League One | 16.12.23 | Stirling Albion FC | - | Annan Athletic | 1:1 | ||||
| League One | 09.11.24 | Queen Of The South | - | Alloa Athletic | 1:1 | ||||
| League One | 19.04.25 | Kelty Hearts | - | Queen Of The South | 1:3 |
Inglaterra