4. Round | 29/08/1998 | Kilmarnock FC | - | Heart of Midlothian | 3:0 | ||||
5. Round | 11/09/1998 | Heart of Midlothian | - | Dundee FC | 0:2 | ||||
6. Round | 19/09/1998 | Dunfermline Athletic | - | Heart of Midlothian | 1:1 | ||||
7. Round | 22/09/1998 | Heart of Midlothian | - | Motherwell FC | 3:0 | ||||
8. Round | 25/09/1998 | Celtic FC | - | Heart of Midlothian | 1:1 | ||||
9. Round | 03/10/1998 | Heart of Midlothian | - | St. Johnstone FC | 1:1 | ||||
10. Round | 16/10/1998 | Rangers FC | - | Heart of Midlothian | 3:0 | ||||
19. Round | 18/12/1998 | Heart of Midlothian | - | Rangers FC | 2:3 | ||||
20. Round | 25/12/1998 | Kilmarnock FC | - | Heart of Midlothian | 1:0 | ||||
26. Round | 29/12/1998 | Heart of Midlothian | - | Dundee FC | 1:2 | ||||
22. Round | 29/01/1999 | Heart of Midlothian | - | Motherwell FC | 0:2 | ||||
29. Round | 02/04/1999 | Heart of Midlothian | - | Kilmarnock FC | 2:2 | ||||
36. Round | 22/05/1999 | Aberdeen FC | - | Heart of Midlothian | 2:5 |