1. Round | 31/07/2021 | Kelty Hearts | - | Cowdenbeath FC | 2:0 | ||||
2. Round | 07/08/2021 | Cowdenbeath FC | - | Elgin City | 3:1 | ||||
4. Round | 21/08/2021 | Stenhousemuir FC | - | Cowdenbeath FC | 1:1 | ||||
5. Round | 28/08/2021 | Cowdenbeath FC | - | Annan Athletic | 1:3 | ||||
3. Round | 31/08/2021 | Cowdenbeath FC | - | Stranraer FC | 1:2 | ||||
6. Round | 11/09/2021 | Albion Rovers | - | Cowdenbeath FC | 2:1 | ||||
7. Round | 18/09/2021 | Cowdenbeath FC | - | Forfar Athletic | 1:1 | ||||
8. Round | 25/09/2021 | Stirling Albion FC | - | Cowdenbeath FC | 4:0 | ||||
9. Round | 01/10/2021 | Edinburgh City FC | - | Cowdenbeath FC | 1:1 | ||||
10. Round | 16/10/2021 | Cowdenbeath FC | - | Stenhousemuir FC | 0:2 | ||||
11. Round | 30/10/2021 | Annan Athletic | - | Cowdenbeath FC | 1:0 |