| 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 | ||||
| League One | 06/01/24 | Annan Athletic | - | Montrose FC | 2:2 | ||||
| League Cup | 16/07/24 | Annan Athletic | - | Bonnyrigg Rose Athletic | 7:6 pso | ||||
| League One | 03/08/24 | Cove Rangers | - | Annan Athletic | 1:3 | ||||
| Chall. Cup | 07/09/24 | Stranraer FC | - | Annan Athletic | 1:5 | ||||
| League One | 26/10/24 | Annan Athletic | - | Queen Of The South | 1:0 | ||||
| League One | 07/12/24 | Annan Athletic | - | Cove Rangers | 1:1 |
Scotland