| 1. Round | 30/07/1999 | St. Johnstone FC | - | Heart of Midlothian | 1:4 | ||||
| 2. Round | 06/08/1999 | Heart of Midlothian | - | Rangers FC | 0:4 | ||||
| 3. Round | 13/08/1999 | Hibernian FC | - | Heart of Midlothian | 1:1 | ||||
| 6. Round | 10/09/1999 | Heart of Midlothian | - | Dundee FC | 4:0 | ||||
| 10. Round | 15/10/1999 | Heart of Midlothian | - | St. Johnstone FC | 1:1 | ||||
| 9. Round | 26/10/1999 | Heart of Midlothian | - | Kilmarnock FC | 2:2 |  |
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| 12. Round | 29/10/1999 | Dundee FC | - | Heart of Midlothian | 1:0 | ||||
| 13. Round | 05/11/1999 | Heart of Midlothian | - | Motherwell FC | 1:1 |  |
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| 17. Round | 04/12/1999 | Heart of Midlothian | - | Dundee United | 3:0 | |
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| 15. Round | 07/12/1999 | Aberdeen FC | - | Heart of Midlothian | 3:1 | ||||
| 19. Round | 18/12/1999 | Heart of Midlothian | - | Hibernian FC | 0:3 | ||||
| 21. Round | 21/01/2000 | Heart of Midlothian | - | Dundee FC | 2:0 | |
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| 34. Round | 05/05/2000 | Heart of Midlothian | - | St. Johnstone FC | 0:0 | ||||
| 35. Round | 12/05/2000 | Rangers FC | - | Heart of Midlothian | 1:0 | ||||
| 36. Round | 20/05/2000 | Heart of Midlothian | - | Hibernian FC | 2:1 | |
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Spain