| 1. Jornada | 02.08.2019 | Dunfermline Athletic | - | Dundee FC | 2:2 | ||||
| 2. Jornada | 10.08.2019 | Queen Of The South | - | Dunfermline Athletic | 1:1 | ||||
| 3. Jornada | 24.08.2019 | Dunfermline Athletic | - | Dundee United | 0:2 | ||||
| 4. Jornada | 31.08.2019 | Arbroath FC | - | Dunfermline Athletic | 1:0 | ||||
| 8. Jornada | 05.10.2019 | Greenock Morton FC | - | Dunfermline Athletic | 1:1 |  |
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| 9. Jornada | 19.10.2019 | Dunfermline Athletic | - | Ayr United | 3:2 | |
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| 10. Jornada | 26.10.2019 | Dundee United | - | Dunfermline Athletic | 2:0 | ||||
| 11. Jornada | 29.10.2019 | Dunfermline Athletic | - | Arbroath FC | 2:0 | ||||
| 12. Jornada | 02.11.2019 | Dunfermline Athletic | - | Queen Of The South | 2:0 |  |
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| 13. Jornada | 09.11.2019 | Alloa Athletic | - | Dunfermline Athletic | 2:1 | ||||
| 15. Jornada | 30.11.2019 | Dunfermline Athletic | - | Partick Thistle | 5:1 | ||||
| 14. Jornada | 03.12.2019 | Ayr United | - | Dunfermline Athletic | 0:1 | ||||
| 18. Jornada | 21.12.2019 | Inverness CT | - | Dunfermline Athletic | 2:0 |
Escocia