| 1. Ronde | 31.07.2021 | Kelty Hearts | - | Cowdenbeath FC | 2:0 |  |
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| 2. Ronde | 07.08.2021 | Cowdenbeath FC | - | Elgin City | 3:1 | ||||
| 4. Ronde | 21.08.2021 | Stenhousemuir FC | - | Cowdenbeath FC | 1:1 |  |
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| 5. Ronde | 28.08.2021 | Cowdenbeath FC | - | Annan Athletic | 1:3 | |
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| 3. Ronde | 31.08.2021 | Cowdenbeath FC | - | Stranraer FC | 1:2 | ||||
| 6. Ronde | 11.09.2021 | Albion Rovers | - | Cowdenbeath FC | 2:1 | ||||
| 7. Ronde | 18.09.2021 | Cowdenbeath FC | - | Forfar Athletic | 1:1 | ||||
| 8. Ronde | 25.09.2021 | Stirling Albion FC | - | Cowdenbeath FC | 4:0 | |
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| 9. Ronde | 01.10.2021 | Edinburgh City FC | - | Cowdenbeath FC | 1:1 | |
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| 10. Ronde | 16.10.2021 | Cowdenbeath FC | - | Stenhousemuir FC | 0:2 | ||||
| 11. Ronde | 30.10.2021 | Annan Athletic | - | Cowdenbeath FC | 1:0 |
Schotland