| 9. Jornada | 01.10.2021 | Edinburgh City FC | - | Cowdenbeath FC | 1:1 | ||||
| 10. Jornada | 16.10.2021 | Cowdenbeath FC | - | Stenhousemuir FC | 0:2 |  |
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| 11. Jornada | 30.10.2021 | Annan Athletic | - | Cowdenbeath FC | 1:0 | ||||
| 12. Jornada | 06.11.2021 | Cowdenbeath FC | - | Kelty Hearts | 0:1 | ||||
| 13. Jornada | 13.11.2021 | Elgin City | - | Cowdenbeath FC | 1:0 | ||||
| 14. Jornada | 20.11.2021 | Forfar Athletic | - | Cowdenbeath FC | 3:0 | ||||
| 15. Jornada | 04.12.2021 | Cowdenbeath FC | - | Stirling Albion FC | 1:0 | ||||
| 16. Jornada | 11.12.2021 | Stranraer FC | - | Cowdenbeath FC | 2:0 | |
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| 17. Jornada | 18.12.2021 | Cowdenbeath FC | - | Albion Rovers | 0:0 | ||||
| 18. Jornada | 22.12.2021 | Cowdenbeath FC | - | Edinburgh City FC | 1:2 |
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