| 4. Ronde | 01.09.2018 | Heart of Midlothian | - | St. Mirren FC | 4:1 | ||||
| 6. Ronde | 22.09.2018 | Heart of Midlothian | - | Livingston FC | 0:0 | ||||
| 8. Ronde | 07.10.2018 | Rangers FC | - | Heart of Midlothian | 3:1 | ||||
| 10. Ronde | 23.10.2018 | Dundee FC | - | Heart of Midlothian | 0:3 | ||||
| 11. Ronde | 31.10.2018 | Heart of Midlothian | - | Hibernian FC | 0:0 | ||||
| 12. Ronde | 03.11.2018 | Celtic FC | - | Heart of Midlothian | 5:0 | ||||
| 13. Ronde | 10.11.2018 | Heart of Midlothian | - | Kilmarnock FC | 0:1 |  |
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| 14. Ronde | 24.11.2018 | St. Mirren FC | - | Heart of Midlothian | 2:0 | ||||
| 16. Ronde | 05.12.2018 | St. Johnstone FC | - | Heart of Midlothian | 2:2 | ||||
| 29. Ronde | 09.03.2019 | Dundee FC | - | Heart of Midlothian | 0:1 | ||||
| 30. Ronde | 16.03.2019 | Hamilton Academical | - | Heart of Midlothian | 1:0 | ||||
| 31. Ronde | 30.03.2019 | Heart of Midlothian | - | Aberdeen FC | 2:1 | ||||
| 32. Ronde | 03.04.2019 | Rangers FC | - | Heart of Midlothian | 3:0 |
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