1. Round | 04/08/2018 | St. Mirren FC | - | Dundee FC | 2:1 | ||||
2. Round | 11/08/2018 | Dundee FC | - | Aberdeen FC | 0:1 | ||||
3. Round | 25/08/2018 | St. Johnstone FC | - | Dundee FC | 1:0 | ||||
4. Round | 01/09/2018 | Dundee FC | - | Motherwell FC | 1:3 | ||||
5. Round | 15/09/2018 | Rangers FC | - | Dundee FC | 4:0 | ||||
6. Round | 22/09/2018 | Dundee FC | - | Hibernian FC | 0:3 | ||||
7. Round | 29/09/2018 | Hamilton Academical | - | Dundee FC | 0:2 | ||||
8. Round | 06/10/2018 | Dundee FC | - | Kilmarnock FC | 1:2 | ||||
9. Round | 20/10/2018 | Livingston FC | - | Dundee FC | 4:0 | ||||
10. Round | 23/10/2018 | Dundee FC | - | Heart of Midlothian | 0:3 |