7. Round | 29/09/2018 | Hamilton Academical | - | Dundee FC | 0:2 | ||||
9. Round | 20/10/2018 | Livingston FC | - | Dundee FC | 4:0 | ||||
10. Round | 23/10/2018 | Dundee FC | - | Heart of Midlothian | 0:3 | ||||
11. Round | 31/10/2018 | Dundee FC | - | Celtic FC | 0:5 | ||||
23. Round | 26/01/2019 | Dundee FC | - | Motherwell FC | 0:1 |