| 23. Round | 26/01/2020 | Heart of Midlothian | - | Rangers FC | 2:1 |  |
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| 24. Round | 01/02/2020 | St. Johnstone FC | - | Heart of Midlothian | 3:3 | |
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| 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 | ||||
| 28. Round | 11/03/2020 | St. Mirren FC | - | Heart of Midlothian | 1:0 |
Northern Ireland
