| 17. Round | 20/02/2021 | Dunfermline Athletic | - | Alloa Athletic | 2:1 |  |
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| 18. Round | 27/02/2021 | Queen Of The South | - | Dunfermline Athletic | 1:0 | ||||
| 20. Round | 13/03/2021 | Dunfermline Athletic | - | Greenock Morton FC | 1:0 | |
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| 21. Round | 20/03/2021 | Dunfermline Athletic | - | Inverness CT | 0:1 |  |
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| 22. Round | 27/03/2021 | Dundee FC | - | Dunfermline Athletic | 3:2 | |
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| 24. Round | 10/04/2021 | Ayr United | - | Dunfermline Athletic | 1:1 | ||||
| 16. Round | 13/04/2021 | Dunfermline Athletic | - | Dundee FC | 0:0 | ||||
| 25. Round | 17/04/2021 | Dunfermline Athletic | - | Queen Of The South | 3:1 | ||||
| 26. Round | 24/04/2021 | Dunfermline Athletic | - | Arbroath FC | 4:3 | |
Scotland