| 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 | 02.01.22 | Stranraer FC | - | Annan Athletic | 1:1 | ||||
| League One | 05.08.23 | Falkirk FC | - | Annan Athletic | 3:0 | ||||
| League One | 28.11.23 | Annan Athletic | - | Hamilton Academical | 1:2 |  |
Écosse