| 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 | ||||
| 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 |  |
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| 9. Round | 26/10/1999 | Heart of Midlothian | - | Kilmarnock FC | 2:2 | ||||
| 12. Round | 29/10/1999 | Dundee FC | - | Heart of Midlothian | 1:0 | ||||
| 17. Round | 04/12/1999 | Heart of Midlothian | - | Dundee United | 3:0 | ||||
| 19. Round | 18/12/1999 | Heart of Midlothian | - | Hibernian FC | 0:3 |
Scotland