| 2. Round | 13/08/2023 | Heart of Midlothian | - | Kilmarnock FC | 0:0 | ||||
| 3. Round | 27/08/2023 | Dundee FC | - | Heart of Midlothian | 1:0 | ||||
| 7. Round | 30/09/2023 | Ross County FC | - | Heart of Midlothian | 0:1 | ||||
| 11. Round | 01/11/2023 | Heart of Midlothian | - | Livingston FC | 1:0 |  |
|||
| 15. Round | 02/12/2023 | Kilmarnock FC | - | Heart of Midlothian | 0:1 | ||||
| 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 | ||||
| 20. Round | 27/12/2023 | Hibernian FC | - | Heart of Midlothian | 0:1 | ||||
| 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 | ||||
| 29. Round | 03/03/2024 | Heart of Midlothian | - | Celtic FC | 2:0 | ||||
| 30. Round | 16/03/2024 | Ross County FC | - | Heart of Midlothian | 2:1 | ||||
| 32. Round | 06/04/2024 | St. Mirren FC | - | Heart of Midlothian | 1:2 |
Scotland