| League Two | 16/04/22 | Forfar Athletic | - | Annan Athletic | 5:1 | ||||
| League Cup | 09/07/22 | Queen Of The South | - | Annan Athletic | 2:3 | ||||
| League Two | 06/08/22 | Annan Athletic | - | Stenhousemuir FC | 2:1 | ||||
| League Two | 28/01/23 | Annan Athletic | - | East Fife FC | 3:0 | ||||
| League Two | 22/04/23 | Stirling Albion FC | - | Annan Athletic | 3:1 |
England