| 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 | ||||
| 4. Jornada | 01.09.2018 | Dunfermline Athletic | - | Inverness CT | 0:3 | ||||
| 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 | ||||
| 24. Jornada | 16.02.2019 | Dunfermline Athletic | - | Inverness CT | 1:0 | ||||
| 27. Jornada | 02.03.2019 | Dunfermline Athletic | - | Queen Of The South | 1:0 | ||||
| 34. Jornada | 20.04.2019 | Queen Of The South | - | Dunfermline Athletic | 2:1 | ||||
| 35. Jornada | 27.04.2019 | Dunfermline Athletic | - | Greenock Morton FC | 0:1 | ||||
| 36. Jornada | 04.05.2019 | Inverness CT | - | Dunfermline Athletic | 1:0 |
Escocia