| 1. Jornada | 04.08.2018 | Dundee United | - | Dunfermline Athletic | 2:3 | ||||
| 2. Jornada | 11.08.2018 | Dunfermline Athletic | - | Ross County FC | 1:3 | ||||
| 3. Jornada | 25.08.2018 | Ayr United | - | Dunfermline Athletic | 4:1 | ||||
| 5. Jornada | 15.09.2018 | Dunfermline Athletic | - | Alloa Athletic | 0:0 |  |
|||
| 6. Jornada | 22.09.2018 | Greenock Morton FC | - | Dunfermline Athletic | 1:1 |  |
|||
| 7. Jornada | 28.09.2018 | Dunfermline Athletic | - | Partick Thistle | 1:0 | ||||
| 8. Jornada | 06.10.2018 | Falkirk FC | - | Dunfermline Athletic | 0:2 | |
|||
| 9. Jornada | 20.10.2018 | Dunfermline Athletic | - | Queen Of The South | 0:1 | ||||
| 10. Jornada | 27.10.2018 | Dunfermline Athletic | - | Dundee United | 0:2 | ||||
| 11. Jornada | 30.10.2018 | Inverness CT | - | Dunfermline Athletic | 2:2 | ||||
| 12. Jornada | 03.11.2018 | Alloa Athletic | - | Dunfermline Athletic | 0:1 | |
|||
| 13. Jornada | 10.11.2018 | Dunfermline Athletic | - | Falkirk FC | 0:1 | ||||
| 36. Jornada | 04.05.2019 | Inverness CT | - | Dunfermline Athletic | 1:0 |
Escocia