| 1. Jornada | 31.07.2021 | Annan Athletic | - | Forfar Athletic | 0:2 | ||||
| 2. Jornada | 07.08.2021 | Stranraer FC | - | Annan Athletic | 0:3 | ||||
| 5. Jornada | 28.08.2021 | Cowdenbeath FC | - | Annan Athletic | 1:3 | ||||
| 8. Jornada | 25.09.2021 | Annan Athletic | - | Edinburgh City FC | 1:3 | ||||
| 9. Jornada | 02.10.2021 | Kelty Hearts | - | Annan Athletic | 2:1 | ||||
| 12. Jornada | 06.11.2021 | Annan Athletic | - | Stranraer FC | 2:2 | ||||
| 14. Jornada | 20.11.2021 | Annan Athletic | - | Albion Rovers | 1:1 |
Inglaterra