| 3. Round | 13/08/1999 | Hibernian FC | - | Heart of Midlothian | 1:1 | ||||
| 4. Round | 21/08/1999 | Heart of Midlothian | - | Aberdeen FC | 3:0 | ||||
| 5. Round | 28/08/1999 | Celtic FC | - | Heart of Midlothian | 4:0 | ||||
| 6. Round | 10/09/1999 | Heart of Midlothian | - | Dundee FC | 4:0 |  |
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| 8. Round | 24/09/1999 | Dundee United | - | Heart of Midlothian | 0:2 | ||||
| 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 | ||||
| 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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| 14. Round | 19/11/1999 | Heart of Midlothian | - | Celtic FC | 1:2 | ||||
| 7. Round | 22/11/1999 | Motherwell FC | - | Heart of Midlothian | 2:1 | ||||
| 16. Round | 26/11/1999 | Kilmarnock FC | - | Heart of Midlothian | 2:2 |  |
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| 17. Round | 04/12/1999 | Heart of Midlothian | - | Dundee United | 3:0 | ||||
| 15. Round | 07/12/1999 | Aberdeen FC | - | Heart of Midlothian | 3:1 |
Scotland