| 1. Round | 04/08/2019 | Aberdeen FC | - | Heart of Midlothian | 3:2 |  |
|||
| 2. Round | 10/08/2019 | Heart of Midlothian | - | Ross County FC | 0:0 | ||||
| 11. Round | 30/10/2019 | St. Johnstone FC | - | Heart of Midlothian | 1:0 | ||||
| 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 | ||||
| 16. Round | 04/12/2019 | Heart of Midlothian | - | Livingston FC | 1:1 | ||||
| 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 | ||||
| 22. Round | 22/01/2020 | Ross County FC | - | Heart of Midlothian | 0:0 | ||||
| 25. Round | 05/02/2020 | Heart of Midlothian | - | Kilmarnock FC | 2:3 | ||||
| 26. Round | 12/02/2020 | Celtic FC | - | Heart of Midlothian | 5:0 |  |
|||
| 27. Round | 15/02/2020 | Heart of Midlothian | - | Hamilton Academical | 2:2 | |
|
||
| 29. Round | 03/03/2020 | Hibernian FC | - | Heart of Midlothian | 1:3 | ||||
| 30. Round | 07/03/2020 | Heart of Midlothian | - | Motherwell FC | 1:1 |
Scotland