| 4. Round | 31/08/2019 | Arbroath FC | - | Dunfermline Athletic | 1:0 | ||||
| 6. Round | 21/09/2019 | Partick Thistle | - | Dunfermline Athletic | 0:3 | ||||
| 10. Round | 26/10/2019 | Dundee United | - | Dunfermline Athletic | 2:0 | ||||
| 11. Round | 29/10/2019 | Dunfermline Athletic | - | Arbroath FC | 2:0 | ||||
| 13. Round | 09/11/2019 | Alloa Athletic | - | Dunfermline Athletic | 2:1 | ||||
| 15. Round | 30/11/2019 | Dunfermline Athletic | - | Partick Thistle | 5:1 | ||||
| 21. Round | 11/01/2020 | Greenock Morton FC | - | Dunfermline Athletic | 3:2 |  |
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| 22. Round | 24/01/2020 | Dunfermline Athletic | - | Dundee FC | 2:0 | |
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| 23. Round | 01/02/2020 | Queen Of The South | - | Dunfermline Athletic | 2:3 |  |
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| 24. Round | 25/02/2020 | Dunfermline Athletic | - | Inverness CT | 1:2 | ||||
| 27. Round | 04/03/2020 | Arbroath FC | - | Dunfermline Athletic | 0:0 | ||||
| 28. Round | 07/03/2020 | Dunfermline Athletic | - | Queen Of The South | 1:1 | ||||
| 25. Round | 10/03/2020 | Partick Thistle | - | Dunfermline Athletic | 1:1 |
England