| 1. Round | 17/10/2020 | Dunfermline Athletic | - | Inverness CT | 3:1 | ||||
| 3. Round | 31/10/2020 | Dunfermline Athletic | - | Queen Of The South | 3:2 | ||||
| 4. Round | 07/11/2020 | Ayr United | - | Dunfermline Athletic | 0:0 |  |
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| 5. Round | 20/11/2020 | Dunfermline Athletic | - | Heart of Midlothian | 2:1 | ||||
| 6. Round | 05/12/2020 | Raith Rovers | - | Dunfermline Athletic | 2:2 | |
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| 7. Round | 12/12/2020 | Dunfermline Athletic | - | Greenock Morton FC | 1:2 | ||||
| 8. Round | 19/12/2020 | Dundee FC | - | Dunfermline Athletic | 3:3 | ||||
| 9. Round | 26/12/2020 | Dunfermline Athletic | - | Arbroath FC | 1:0 | ||||
| 10. Round | 29/12/2020 | Inverness CT | - | Dunfermline Athletic | 1:1 | ||||
| 11. Round | 03/02/2021 | Dunfermline Athletic | - | Raith Rovers | 4:1 | ||||
| 15. Round | 06/02/2021 | Arbroath FC | - | Dunfermline Athletic | 2:0 | ||||
| 18. Round | 27/02/2021 | Queen Of The South | - | Dunfermline Athletic | 1:0 | ||||
| 25. Round | 17/04/2021 | Dunfermline Athletic | - | Queen Of The South | 3:1 | ||||
| 26. Round | 24/04/2021 | Dunfermline Athletic | - | Arbroath FC | 4:3 | ||||
| 27. Round | 30/04/2021 | Alloa Athletic | - | Dunfermline Athletic | 1:0 |
Scotland