2. Round | 10/08/2019 | Queen Of The South | - | Dunfermline Athletic | 1:1 | ||||
3. Round | 24/08/2019 | Dunfermline Athletic | - | Dundee United | 0:2 | ||||
8. Round | 05/10/2019 | Greenock Morton FC | - | Dunfermline Athletic | 1:1 | ||||
16. Round | 07/12/2019 | Dunfermline Athletic | - | Greenock Morton FC | 3:1 |