Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 13.07.2021 |  | Group F | Annan Athletic - Queen Of The South | - | 1:3 | 300 |
| 20.07.2021 | | Group F | Annan Athletic - Queen's Park FC | - | 1:2 | 300 |
| 31.07.2021 |  | Matchday 1 | Annan Athletic - Forfar Athletic | - FOR | 0:2 | 300 |
| 14.08.2021 | | Matchday 3 | Annan Athletic - Stirling Albion | - Sti | 3:1 | 295 |
| 11.09.2021 | | Matchday 6 | Annan Athletic - Stenhousemuir | - Ste | 1:2 | Unter Ausschluss der Öffentlichkeit. |
| 25.09.2021 | | Matchday 8 | Annan Athletic - Edinburgh City | - EC | 1:3 | 324 |
| 30.10.2021 | | Matchday 11 | Annan Athletic - Cowdenbeath FC | - | 1:0 | 187 |
| 06.11.2021 | | Matchday 12 | Annan Athletic - Stranraer FC | - Str | 2:2 | 305 |
| 20.11.2021 | | Matchday 14 | Annan Athletic - Albion Rovers | - ALB | 1:1 | 284 |
| 11.12.2021 | | Matchday 16 | Annan Athletic - Elgin City | - Elg | 4:1 | 221 |
| 26.12.2021 | | Matchday 18 | Annan Athletic - Kelty Hearts | - KH | 5:1 | 372 |