| 1. Jornada | 04.08.2019 | Aberdeen FC | - | Heart of Midlothian | 3:2 |  |
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| 2. Jornada | 10.08.2019 | Heart of Midlothian | - | Ross County FC | 0:0 | ||||
| 11. Jornada | 30.10.2019 | St. Johnstone FC | - | Heart of Midlothian | 1:0 | ||||
| 13. Jornada | 09.11.2019 | Heart of Midlothian | - | St. Mirren FC | 5:2 | |
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| 14. Jornada | 23.11.2019 | Kilmarnock FC | - | Heart of Midlothian | 3:0 | ||||
| 15. Jornada | 01.12.2019 | Rangers FC | - | Heart of Midlothian | 5:0 | ||||
| 16. Jornada | 04.12.2019 | Heart of Midlothian | - | Livingston FC | 1:1 | ||||
| 17. Jornada | 07.12.2019 | Motherwell FC | - | Heart of Midlothian | 1:0 | ||||
| 18. Jornada | 14.12.2019 | Heart of Midlothian | - | St. Johnstone FC | 0:1 | ||||
| 22. Jornada | 22.01.2020 | Ross County FC | - | Heart of Midlothian | 0:0 | ||||
| 25. Jornada | 05.02.2020 | Heart of Midlothian | - | Kilmarnock FC | 2:3 | ||||
| 26. Jornada | 12.02.2020 | Celtic FC | - | Heart of Midlothian | 5:0 |  |
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| 27. Jornada | 15.02.2020 | Heart of Midlothian | - | Hamilton Academical | 2:2 | |
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| 29. Jornada | 03.03.2020 | Hibernian FC | - | Heart of Midlothian | 1:3 | ||||
| 30. Jornada | 07.03.2020 | Heart of Midlothian | - | Motherwell FC | 1:1 |
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