| 1. Journée | 02.08.2019 | Dunfermline Athletic | - | Dundee FC | 2:2 |  |
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| 2. Journée | 10.08.2019 | Queen Of The South | - | Dunfermline Athletic | 1:1 | ||||
| 3. Journée | 24.08.2019 | Dunfermline Athletic | - | Dundee United | 0:2 | ||||
| 4. Journée | 31.08.2019 | Arbroath FC | - | Dunfermline Athletic | 1:0 | ||||
| 5. Journée | 14.09.2019 | Dunfermline Athletic | - | Inverness CT | 0:1 | ||||
| 7. Journée | 28.09.2019 | Dunfermline Athletic | - | Alloa Athletic | 1:1 | ||||
| 9. Journée | 19.10.2019 | Dunfermline Athletic | - | Ayr United | 3:2 |
Angleterre