| 7. Jornada | 23.09.1998 | Heart of Midlothian | - | Motherwell FC | 3:0 | ||||
| 8. Jornada | 26.09.1998 | Celtic FC | - | Heart of Midlothian | 1:1 | ||||
| 15. Jornada | 21.11.1998 | Heart of Midlothian | - | Dunfermline Athletic | 2:1 | ||||
| 21. Jornada | 02.01.1999 | Dunfermline Athletic | - | Heart of Midlothian | 0:0 | ||||
| 22. Jornada | 30.01.1999 | Heart of Midlothian | - | Motherwell FC | 0:2 | ||||
| 23. Jornada | 06.02.1999 | Celtic FC | - | Heart of Midlothian | 3:0 | ||||
| 24. Jornada | 20.02.1999 | Heart of Midlothian | - | St. Johnstone FC | 0:2 | ||||
| 25. Jornada | 27.02.1999 | Heart of Midlothian | - | Aberdeen FC | 0:2 | ||||
| 35. Jornada | 15.05.1999 | Heart of Midlothian | - | Dundee United | 4:1 | ||||
| 36. Jornada | 23.05.1999 | Aberdeen FC | - | Heart of Midlothian | 2:5 |
Escocia