| 1. Ronde | 31.07.1999 | St. Johnstone FC | - | Heart of Midlothian | 1:4 | ||||
| 2. Ronde | 07.08.1999 | Heart of Midlothian | - | Rangers FC | 0:4 | ||||
| 3. Ronde | 14.08.1999 | Hibernian FC | - | Heart of Midlothian | 1:1 | ||||
| 6. Ronde | 11.09.1999 | Heart of Midlothian | - | Dundee FC | 4:0 | ||||
| 10. Ronde | 16.10.1999 | Heart of Midlothian | - | St. Johnstone FC | 1:1 | ||||
| 9. Ronde | 27.10.1999 | Heart of Midlothian | - | Kilmarnock FC | 2:2 |  |
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| 12. Ronde | 30.10.1999 | Dundee FC | - | Heart of Midlothian | 1:0 | ||||
| 13. Ronde | 06.11.1999 | Heart of Midlothian | - | Motherwell FC | 1:1 |  |
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| 17. Ronde | 05.12.1999 | Heart of Midlothian | - | Dundee United | 3:0 | |
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| 15. Ronde | 08.12.1999 | Aberdeen FC | - | Heart of Midlothian | 3:1 | ||||
| 19. Ronde | 19.12.1999 | Heart of Midlothian | - | Hibernian FC | 0:3 | ||||
| 21. Ronde | 22.01.2000 | Heart of Midlothian | - | Dundee FC | 2:0 | |
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| 34. Ronde | 06.05.2000 | Heart of Midlothian | - | St. Johnstone FC | 0:0 | ||||
| 35. Ronde | 13.05.2000 | Rangers FC | - | Heart of Midlothian | 1:0 | ||||
| 36. Ronde | 21.05.2000 | Heart of Midlothian | - | Hibernian FC | 2:1 | |
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