| 1. Jornada | 31.07.1999 | Hibernian FC | - | Motherwell FC | 2:2 | ||||
| 2. Jornada | 08.08.1999 | Dundee FC | - | Hibernian FC | 3:4 | ||||
| 3. Jornada | 14.08.1999 | Hibernian FC | - | Heart of Midlothian | 1:1 |  |
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| 4. Jornada | 21.08.1999 | St. Johnstone FC | - | Hibernian FC | 1:1 | |
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| 5. Jornada | 28.08.1999 | Hibernian FC | - | Rangers FC | 0:1 | ||||
| 6. Jornada | 11.09.1999 | Dundee United | - | Hibernian FC | 3:1 | ||||
| 7. Jornada | 19.09.1999 | Hibernian FC | - | Kilmarnock FC | 0:3 | ||||
| 8. Jornada | 25.09.1999 | Hibernian FC | - | Celtic FC | 0:2 | |
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| 9. Jornada | 02.10.1999 | Aberdeen FC | - | Hibernian FC | 2:2 | ||||
| 20. Jornada | 27.12.1999 | Hibernian FC | - | Kilmarnock FC | 2:2 | ||||
| 30. Jornada | 03.05.2000 | Rangers FC | - | Hibernian FC | 5:2 | ||||
| 34. Jornada | 06.05.2000 | Motherwell FC | - | Hibernian FC | 2:0 | ||||
| 26. Jornada | 14.05.2000 | Dundee FC | - | Hibernian FC | 1:0 |
Escocia