3. Round | 21/08/1998 | Heart of Midlothian | - | Aberdeen FC | 2:0 | ||||
4. Round | 29/08/1998 | Kilmarnock FC | - | Heart of Midlothian | 3:0 | ||||
5. Round | 11/09/1998 | Heart of Midlothian | - | Dundee FC | 0:2 | ||||
9. Round | 03/10/1998 | Heart of Midlothian | - | St. Johnstone FC | 1:1 | ||||
11. Round | 23/10/1998 | Heart of Midlothian | - | Dundee United | 0:1 | ||||
12. Round | 30/10/1998 | Dundee FC | - | Heart of Midlothian | 1:0 | ||||
13. Round | 06/11/1998 | Heart of Midlothian | - | Kilmarnock FC | 2:1 | ||||
14. Round | 13/11/1998 | Motherwell FC | - | Heart of Midlothian | 3:2 | ||||
19. Round | 18/12/1998 | Heart of Midlothian | - | Rangers FC | 2:3 | ||||
20. Round | 25/12/1998 | Kilmarnock FC | - | Heart of Midlothian | 1:0 | ||||
23. Round | 05/02/1999 | Celtic FC | - | Heart of Midlothian | 3:0 | ||||
24. Round | 19/02/1999 | Heart of Midlothian | - | St. Johnstone FC | 0:2 |