| League Two | 13.11.21 | Stenhousemuir FC | - | Annan Athletic | 2:0 | ||||
| League Two | 03.12.21 | Edinburgh City FC | - | Annan Athletic | 0:1 | ||||
| League Two | 23.12.22 | Annan Athletic | - | Albion Rovers | 5:1 |  |
|||
| League Two | 29.04.23 | Annan Athletic | - | Bonnyrigg Rose Athletic | 0:0 | ||||
| League One | 05.08.23 | Falkirk FC | - | Annan Athletic | 3:0 | ||||
| League One | 28.11.23 | Annan Athletic | - | Hamilton Academical | 1:2 | ||||
| League One | 27.01.24 | Annan Athletic | - | Edinburgh City | 3:0 | ||||
| League Two | 04.01.25 | Clyde FC | - | Stirling Albion FC | 2:0 |
Escocia