1. Round | 04/08/2018 | Dundee United | - | Dunfermline Athletic | 2:3 | ||||
2. Round | 11/08/2018 | Dunfermline Athletic | - | Ross County FC | 1:3 | ||||
3. Round | 25/08/2018 | Ayr United | - | Dunfermline Athletic | 4:1 | ||||
5. Round | 15/09/2018 | Dunfermline Athletic | - | Alloa Athletic | 0:0 | ||||
6. Round | 22/09/2018 | Greenock Morton FC | - | Dunfermline Athletic | 1:1 | ||||
7. Round | 28/09/2018 | Dunfermline Athletic | - | Partick Thistle | 1:0 | ||||
8. Round | 06/10/2018 | Falkirk FC | - | Dunfermline Athletic | 0:2 | ||||
9. Round | 20/10/2018 | Dunfermline Athletic | - | Queen Of The South | 0:1 | ||||
10. Round | 27/10/2018 | Dunfermline Athletic | - | Dundee United | 0:2 | ||||
11. Round | 30/10/2018 | Inverness CT | - | Dunfermline Athletic | 2:2 | ||||
12. Round | 03/11/2018 | Alloa Athletic | - | Dunfermline Athletic | 0:1 | ||||
13. Round | 10/11/2018 | Dunfermline Athletic | - | Falkirk FC | 0:1 | ||||
36. Round | 04/05/2019 | Inverness CT | - | Dunfermline Athletic | 1:0 |