| League Two | 03/12/22 | East Fife FC | - | Annan Athletic | 1:3 |  |
|||
| League Two | 25/03/23 | Annan Athletic | - | Stranraer FC | 0:0 |  |
|||
| League Two | 06/05/23 | Stenhousemuir FC | - | Annan Athletic | 2:1 | |
|||
| League One | 03/02/24 | Annan Athletic | - | Alloa Athletic | 2:3 | ||||
| League One | 16/03/24 | Montrose FC | - | Annan Athletic | 1:1 |
England