| League Two | 18/03/23 | Forfar Athletic | - | Annan Athletic | 2:1 | ||||
| League One | 13/02/24 | Alloa Athletic | - | Annan Athletic | 2:1 | ||||
| League One | 06/04/24 | Annan Athletic | - | Hamilton Academical | 1:3 | ||||
| League One | 23/11/24 | Montrose FC | - | Annan Athletic | 2:1 | ||||
| League One | 22/03/25 | Montrose FC | - | Annan Athletic | 3:1 |
Scotland