| 3. Round | 25/08/2018 | Kilmarnock FC | - | Heart of Midlothian | 0:1 | ||||
| 4. Round | 01/09/2018 | Heart of Midlothian | - | St. Mirren FC | 4:1 | ||||
| 5. Round | 15/09/2018 | Motherwell FC | - | Heart of Midlothian | 0:1 | ||||
| 6. Round | 22/09/2018 | Heart of Midlothian | - | Livingston FC | 0:0 | ||||
| 7. Round | 29/09/2018 | Heart of Midlothian | - | St. Johnstone FC | 2:1 |  |
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| 8. Round | 07/10/2018 | Rangers FC | - | Heart of Midlothian | 3:1 | |
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| 9. Round | 20/10/2018 | Heart of Midlothian | - | Aberdeen FC | 2:1 | ||||
| 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 | ||||
| 14. Round | 24/11/2018 | St. Mirren FC | - | Heart of Midlothian | 2:0 |
Ireland