| League Two | 08.10.22 | Stenhousemuir FC | - | Annan Athletic | 2:2 | ||||
| League Two | 18.02.23 | Annan Athletic | - | Stirling Albion FC | 2:2 | ||||
| League Two | 08.04.23 | Annan Athletic | - | Dumbarton FC | 3:1 | ||||
| Chall. Cup | 07.09.24 | Stranraer FC | - | Annan Athletic | 1:5 | ||||
| League One | 07.12.24 | Annan Athletic | - | Cove Rangers | 1:1 |
Inglaterra