| 2. Round | 10/08/2019 | Heart of Midlothian | - | Ross County FC | 0:0 | ||||
| 3. Round | 25/08/2019 | Celtic FC | - | Heart of Midlothian | 3:1 | ||||
| 4. Round | 31/08/2019 | Heart of Midlothian | - | Hamilton Academical | 2:2 | ||||
| 7. Round | 28/09/2019 | St. Mirren FC | - | Heart of Midlothian | 0:0 | ||||
| 9. Round | 20/10/2019 | Heart of Midlothian | - | Rangers FC | 1:1 |  |
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| 11. Round | 30/10/2019 | St. Johnstone FC | - | Heart of Midlothian | 1:0 | |
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| 13. Round | 09/11/2019 | Heart of Midlothian | - | St. Mirren FC | 5:2 | ||||
| 14. Round | 23/11/2019 | Kilmarnock FC | - | Heart of Midlothian | 3:0 | ||||
| 15. Round | 01/12/2019 | Rangers FC | - | Heart of Midlothian | 5:0 | ||||
| 19. Round | 21/12/2019 | Hamilton Academical | - | Heart of Midlothian | 2:1 | ||||
| 20. Round | 26/12/2019 | Heart of Midlothian | - | Hibernian FC | 0:2 | ||||
| 23. Round | 26/01/2020 | Heart of Midlothian | - | Rangers FC | 2:1 | ||||
| 24. Round | 01/02/2020 | St. Johnstone FC | - | Heart of Midlothian | 3:3 | ||||
| 25. Round | 05/02/2020 | Heart of Midlothian | - | Kilmarnock FC | 2:3 |
England