| 4. Round | 31/08/2019 | Arbroath FC | - | Dunfermline Athletic | 1:0 | ||||
| 5. Round | 14/09/2019 | Dunfermline Athletic | - | Inverness CT | 0:1 | ||||
| 6. Round | 21/09/2019 | Partick Thistle | - | Dunfermline Athletic | 0:3 | ||||
| 7. Round | 28/09/2019 | Dunfermline Athletic | - | Alloa Athletic | 1:1 |  |
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| 8. Round | 05/10/2019 | Greenock Morton FC | - | Dunfermline Athletic | 1:1 | |
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| 9. Round | 19/10/2019 | Dunfermline Athletic | - | Ayr United | 3:2 | ||||
| 10. Round | 26/10/2019 | Dundee United | - | Dunfermline Athletic | 2:0 | ||||
| 11. Round | 29/10/2019 | Dunfermline Athletic | - | Arbroath FC | 2:0 | ||||
| 15. Round | 30/11/2019 | Dunfermline Athletic | - | Partick Thistle | 5:1 | ||||
| 14. Round | 03/12/2019 | Ayr United | - | Dunfermline Athletic | 0:1 | ||||
| 16. Round | 07/12/2019 | Dunfermline Athletic | - | Greenock Morton FC | 3:1 | ||||
| 17. Round | 14/12/2019 | Dundee FC | - | Dunfermline Athletic | 4:3 |
Scotland