| 2. Jornada | 10.08.2019 | Heart of Midlothian | - | Ross County FC | 0:0 | ||||
| 3. Jornada | 25.08.2019 | Celtic FC | - | Heart of Midlothian | 3:1 | ||||
| 4. Jornada | 31.08.2019 | Heart of Midlothian | - | Hamilton Academical | 2:2 | ||||
| 7. Jornada | 28.09.2019 | St. Mirren FC | - | Heart of Midlothian | 0:0 | ||||
| 9. Jornada | 20.10.2019 | Heart of Midlothian | - | Rangers FC | 1:1 |  |
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| 11. Jornada | 30.10.2019 | St. Johnstone FC | - | Heart of Midlothian | 1:0 | |
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| 13. Jornada | 09.11.2019 | Heart of Midlothian | - | St. Mirren FC | 5:2 | ||||
| 14. Jornada | 23.11.2019 | Kilmarnock FC | - | Heart of Midlothian | 3:0 | ||||
| 15. Jornada | 01.12.2019 | Rangers FC | - | Heart of Midlothian | 5:0 | ||||
| 19. Jornada | 21.12.2019 | Hamilton Academical | - | Heart of Midlothian | 2:1 | ||||
| 20. Jornada | 26.12.2019 | Heart of Midlothian | - | Hibernian FC | 0:2 | ||||
| 23. Jornada | 26.01.2020 | Heart of Midlothian | - | Rangers FC | 2:1 | ||||
| 24. Jornada | 01.02.2020 | St. Johnstone FC | - | Heart of Midlothian | 3:3 | ||||
| 25. Jornada | 05.02.2020 | Heart of Midlothian | - | Kilmarnock FC | 2:3 |
Inglaterra