| 5. Round | 14/09/2019 | Heart of Midlothian | - | Motherwell FC | 2:3 | ||||
| 7. Round | 28/09/2019 | St. Mirren FC | - | Heart of Midlothian | 0:0 | ||||
| 8. Round | 05/10/2019 | Heart of Midlothian | - | Kilmarnock FC | 0:1 | ||||
| 9. Round | 20/10/2019 | Heart of Midlothian | - | Rangers FC | 1:1 |  |
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| 10. Round | 26/10/2019 | Livingston FC | - | Heart of Midlothian | 0:0 | ||||
| 11. Round | 30/10/2019 | St. Johnstone FC | - | Heart of Midlothian | 1:0 | |
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| 16. Round | 04/12/2019 | Heart of Midlothian | - | Livingston FC | 1:1 |  |
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| 17. Round | 07/12/2019 | Motherwell FC | - | Heart of Midlothian | 1:0 | ||||
| 18. Round | 14/12/2019 | Heart of Midlothian | - | St. Johnstone FC | 0:1 | ||||
| 12. Round | 18/12/2019 | Heart of Midlothian | - | Celtic FC | 0:2 | |
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| 19. Round | 21/12/2019 | Hamilton Academical | - | Heart of Midlothian | 2:1 | |
Scotland