| 4. Round | 01/09/2018 | Heart of Midlothian | - | St. Mirren FC | 4:1 | ||||
| 6. Round | 22/09/2018 | Heart of Midlothian | - | Livingston FC | 0:0 | ||||
| 8. Round | 07/10/2018 | Rangers FC | - | Heart of Midlothian | 3:1 | ||||
| 10. Round | 23/10/2018 | Dundee FC | - | Heart of Midlothian | 0:3 | ||||
| 11. Round | 31/10/2018 | Heart of Midlothian | - | Hibernian FC | 0:0 | ||||
| 12. Round | 03/11/2018 | Celtic FC | - | Heart of Midlothian | 5:0 | ||||
| 13. Round | 10/11/2018 | Heart of Midlothian | - | Kilmarnock FC | 0:1 |  |
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| 14. Round | 24/11/2018 | St. Mirren FC | - | Heart of Midlothian | 2:0 | ||||
| 16. Round | 05/12/2018 | St. Johnstone FC | - | Heart of Midlothian | 2:2 | ||||
| 29. Round | 09/03/2019 | Dundee FC | - | Heart of Midlothian | 0:1 | ||||
| 30. Round | 16/03/2019 | Hamilton Academical | - | Heart of Midlothian | 1:0 | ||||
| 31. Round | 30/03/2019 | Heart of Midlothian | - | Aberdeen FC | 2:1 | ||||
| 32. Round | 03/04/2019 | Rangers FC | - | Heart of Midlothian | 3:0 |
Scotland