| 1. Jornada | 31.07.1999 | St. Johnstone FC | - | Heart of Midlothian | 1:4 | ||||
| 2. Jornada | 07.08.1999 | Heart of Midlothian | - | Rangers FC | 0:4 | ||||
| 3. Jornada | 14.08.1999 | Hibernian FC | - | Heart of Midlothian | 1:1 | ||||
| 6. Jornada | 11.09.1999 | Heart of Midlothian | - | Dundee FC | 4:0 | ||||
| 8. Jornada | 25.09.1999 | Dundee United | - | Heart of Midlothian | 0:2 | ||||
| 10. Jornada | 16.10.1999 | Heart of Midlothian | - | St. Johnstone FC | 1:1 |  |
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| 9. Jornada | 27.10.1999 | Heart of Midlothian | - | Kilmarnock FC | 2:2 | ||||
| 12. Jornada | 30.10.1999 | Dundee FC | - | Heart of Midlothian | 1:0 | ||||
| 17. Jornada | 05.12.1999 | Heart of Midlothian | - | Dundee United | 3:0 | ||||
| 19. Jornada | 19.12.1999 | Heart of Midlothian | - | Hibernian FC | 0:3 |
Escocia