| 12. Round | 23/01/2024 | Heart of Midlothian | - | Dundee FC | 3:2 |  |
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| 9. Round | 30/01/2024 | Aberdeen FC | - | Dundee FC | 1:1 | ||||
| 25. Round | 07/02/2024 | St. Mirren FC | - | Dundee FC | 2:0 | ||||
| 26. Round | 17/02/2024 | Dundee FC | - | Ross County FC | 2:0 | ||||
| 27. Round | 24/02/2024 | Hibernian FC | - | Dundee FC | 2:1 | ||||
| 28. Round | 28/02/2024 | Celtic FC | - | Dundee FC | 7:1 | ||||
| 29. Round | 02/03/2024 | Dundee FC | - | Kilmarnock FC | 2:2 | ||||
| 19. Round | 13/03/2024 | Dundee FC | - | Aberdeen FC | 1:0 | |
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| 33. Round | 13/04/2024 | Aberdeen FC | - | Dundee FC | 0:0 | ||||
| 30. Round | 17/04/2024 | Dundee FC | - | Rangers FC | 0:0 |
England