| 17. Round | 09/12/2023 | Aberdeen FC | - | Heart of Midlothian | 2:1 | ||||
| 18. Round | 16/12/2023 | Celtic FC | - | Heart of Midlothian | 0:2 | ||||
| 19. Round | 23/12/2023 | Heart of Midlothian | - | St. Mirren FC | 2:0 |  |
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| 21. Round | 30/12/2023 | Heart of Midlothian | - | Ross County FC | 2:2 | ||||
| 22. Round | 02/01/2024 | Livingston FC | - | Heart of Midlothian | 1:2 | ||||
| 12. Round | 23/01/2024 | Heart of Midlothian | - | Dundee FC | 3:2 | ||||
| 23. Round | 27/01/2024 | Heart of Midlothian | - | Aberdeen FC | 2:0 | ||||
| 24. Round | 03/02/2024 | Dundee FC | - | Heart of Midlothian | 2:3 | ||||
| 25. Round | 07/02/2024 | St. Johnstone FC | - | Heart of Midlothian | 0:1 |
Scotland