| 1. Round | 17/10/2020 | Dunfermline Athletic | - | Inverness CT | 3:1 | ||||
| 2. Round | 24/10/2020 | Alloa Athletic | - | Dunfermline Athletic | 1:4 | ||||
| 3. Round | 31/10/2020 | Dunfermline Athletic | - | Queen Of The South | 3:2 | ||||
| 4. Round | 07/11/2020 | Ayr United | - | Dunfermline Athletic | 0:0 | ||||
| 5. Round | 20/11/2020 | Dunfermline Athletic | - | Heart of Midlothian | 2:1 | ||||
| 6. Round | 05/12/2020 | Raith Rovers | - | Dunfermline Athletic | 2:2 | ||||
| 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 |  |
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| 13. Round | 15/01/2021 | Greenock Morton FC | - | Dunfermline Athletic | 0:0 | ||||
| 14. Round | 23/01/2021 | Dunfermline Athletic | - | Ayr United | 0:0 | ||||
| 20. Round | 13/03/2021 | Dunfermline Athletic | - | Greenock Morton FC | 1:0 |
Scotland