| 19. Ronde | 19.12.1999 | Heart of Midlothian | - | Hibernian FC | 0:3 | ||||
| 11. Ronde | 22.12.1999 | Rangers FC | - | Heart of Midlothian | 1:0 | ||||
| 22. Ronde | 05.02.2000 | Celtic FC | - | Heart of Midlothian | 2:3 |  |
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| 24. Ronde | 26.02.2000 | Heart of Midlothian | - | Kilmarnock FC | 0:0 | ||||
| 20. Ronde | 01.03.2000 | Motherwell FC | - | Heart of Midlothian | 0:2 | ||||
| 25. Ronde | 04.03.2000 | Dundee United | - | Heart of Midlothian | 0:1 | ||||
| 29. Ronde | 01.04.2000 | Dundee FC | - | Heart of Midlothian | 0:0 | ||||
| 30. Ronde | 08.04.2000 | Heart of Midlothian | - | Celtic FC | 1:0 | ||||
| 26. Ronde | 12.04.2000 | Heart of Midlothian | - | Rangers FC | 1:2 | ||||
| 31. Ronde | 15.04.2000 | Aberdeen FC | - | Heart of Midlothian | 1:2 | ||||
| 33. Ronde | 29.04.2000 | Kilmarnock FC | - | Heart of Midlothian | 0:1 |
Engeland