1. Round | 04/08/2018 | Hamilton Academical | - | Heart of Midlothian | 1:4 | ||||
2. Round | 11/08/2018 | Heart of Midlothian | - | Celtic FC | 1:0 | ||||
3. Round | 25/08/2018 | Kilmarnock FC | - | Heart of Midlothian | 0:1 | ||||
4. Round | 01/09/2018 | Heart of Midlothian | - | St. Mirren FC | 4:1 | ||||
5. Round | 15/09/2018 | Motherwell FC | - | Heart of Midlothian | 0:1 | ||||
8. Round | 07/10/2018 | Rangers FC | - | Heart of Midlothian | 3:1 | ||||
25. Round | 06/02/2019 | Heart of Midlothian | - | Livingston FC | 0:0 | ||||
26. Round | 17/02/2019 | Motherwell FC | - | Heart of Midlothian | 2:1 | ||||
27. Round | 23/02/2019 | Heart of Midlothian | - | St. Mirren FC | 1:1 | ||||
28. Round | 27/02/2019 | Heart of Midlothian | - | Celtic FC | 1:2 | ||||
29. Round | 09/03/2019 | Dundee FC | - | Heart of Midlothian | 0:1 | ||||
30. Round | 16/03/2019 | Hamilton Academical | - | Heart of Midlothian | 1:0 | ||||
31. Round | 30/03/2019 | Heart of Midlothian | - | Aberdeen FC | 2:1 | ||||
33. Round | 06/04/2019 | Heart of Midlothian | - | Hibernian FC | 1:2 |