Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 10.07.2021 |  | Group D | Cowdenbeath FC - Raith Rovers | - Rai | 0:1 | 778 |
| 17.07.2021 | | Group D | Cowdenbeath FC - Brechin City FC | - | 3:2 | 245 |
| 07.08.2021 |  | Matchday 2 | Cowdenbeath FC - Elgin City | - Elg | 3:1 | 307 |
| 28.08.2021 | | Matchday 5 | Cowdenbeath FC - Annan Athletic | - | 1:3 | Unter Ausschluss der Öffentlichkeit. |
| 31.08.2021 | | Matchday 3 | Cowdenbeath FC - Stranraer FC | - Str | 1:2 | Unter Ausschluss der Öffentlichkeit. |
| 18.09.2021 | | Matchday 7 | Cowdenbeath FC - Forfar Athletic | - FOR | 1:1 | 323 |
| 16.10.2021 | | Matchday 10 | Cowdenbeath FC - Stenhousemuir | - Ste | 0:2 | 293 |
| 06.11.2021 | | Matchday 12 | Cowdenbeath FC - Kelty Hearts | - KH | 0:1 | 727 |
| 04.12.2021 | | Matchday 15 | Cowdenbeath FC - Stirling Albion | - Sti | 1:0 | 313 |
| 18.12.2021 | | Matchday 17 | Cowdenbeath FC - Albion Rovers | - ALB | 0:0 | 266 |
| 22.12.2021 | | Matchday 18 | Cowdenbeath FC - Edinburgh City | - EC | 1:2 | 221 |