Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 08.01.2022 |  | Matchday 20 | Cowdenbeath FC - Annan Athletic | - | 1:3 | 243 |
| 22.01.2022 | | Matchday 22 | Cowdenbeath FC - Stranraer FC | - Str | 0:1 | 331 |
| 19.02.2022 | | Matchday 26 | Cowdenbeath FC - Elgin City | - Elg | 2:0 | 441 |
| 15.03.2022 | | Matchday 25 | Cowdenbeath FC - Forfar Athletic | - FOR | 1:2 | 246 |
| 19.03.2022 | | Matchday 30 | Cowdenbeath FC - Stenhousemuir | - Ste | 1:1 | 455 |
| 02.04.2022 | | Matchday 32 | Cowdenbeath FC - Stirling Albion | - Sti | 0:0 | 416 |
| 16.04.2022 | | Matchday 34 | Cowdenbeath FC - Edinburgh City | - EC | 0:0 | 328 |
| 30.04.2022 | | Matchday 36 | Cowdenbeath FC - Albion Rovers | - ALB | 0:1 | 411 |
| 14.05.2022 |  | Final 2nd leg | Cowdenbeath FC - Bonnyrigg Rose | - BRA | 0:1 | |
| 09.07.2022 |  | Group E | Cowdenbeath FC - Airdrieonians | - AIR | 0:3 | 345 |
| 16.07.2022 | | Group E | Cowdenbeath FC - St. Mirren | - STM | 0:2 | 638 |