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 | ||||
5. Round | 15/09/2018 | Rangers FC | - | Dundee FC | 4:0 | ||||
9. Round | 20/10/2018 | Livingston FC | - | Dundee FC | 4:0 | ||||
11. Round | 31/10/2018 | Dundee FC | - | Celtic FC | 0:5 | ||||
12. Round | 03/11/2018 | Motherwell FC | - | Dundee FC | 1:0 | ||||
13. Round | 10/11/2018 | Dundee FC | - | St. Mirren FC | 1:1 | ||||
14. Round | 24/11/2018 | Hibernian FC | - | Dundee FC | 2:2 |