1. Round | 31/07/2021 | East Fife FC | - | Queen's Park FC | 1:1 | ||||
2. Round | 07/08/2021 | Alloa Athletic | - | East Fife FC | 3:1 | ||||
4. Round | 21/08/2021 | East Fife FC | - | Montrose FC | 0:2 | ||||
6. Round | 11/09/2021 | Dumbarton FC | - | East Fife FC | 5:0 | ||||
7. Round | 18/09/2021 | Airdrieonians FC | - | East Fife FC | 3:0 | ||||
8. Round | 25/09/2021 | East Fife FC | - | Clyde FC | 0:2 | ||||
9. Round | 02/10/2021 | Falkirk FC | - | East Fife FC | 2:1 | ||||
10. Round | 16/10/2021 | East Fife FC | - | Cove Rangers | 4:2 |