| 2. Jornada | 07.08.1999 | Heart of Midlothian | - | Rangers FC | 0:4 | ||||
| 5. Jornada | 29.08.1999 | Celtic FC | - | Heart of Midlothian | 4:0 |  |
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| 6. Jornada | 11.09.1999 | Heart of Midlothian | - | Dundee FC | 4:0 | ||||
| 12. Jornada | 30.10.1999 | Dundee FC | - | Heart of Midlothian | 1:0 | ||||
| 13. Jornada | 06.11.1999 | Heart of Midlothian | - | Motherwell FC | 1:1 | ||||
| 14. Jornada | 20.11.1999 | Heart of Midlothian | - | Celtic FC | 1:2 | ||||
| 7. Jornada | 23.11.1999 | Motherwell FC | - | Heart of Midlothian | 2:1 | ||||
| 16. Jornada | 27.11.1999 | Kilmarnock FC | - | Heart of Midlothian | 2:2 |  |
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| 15. Jornada | 08.12.1999 | Aberdeen FC | - | Heart of Midlothian | 3:1 | ||||
| 11. Jornada | 22.12.1999 | Rangers FC | - | Heart of Midlothian | 1:0 | ||||
| 21. Jornada | 22.01.2000 | Heart of Midlothian | - | Dundee FC | 2:0 | ||||
| 34. Jornada | 06.05.2000 | Heart of Midlothian | - | St. Johnstone FC | 0:0 |
Escocia