| 8. Ronde | 25.09.1999 | Hibernian FC | - | Celtic FC | 0:2 | ||||
| 9. Ronde | 02.10.1999 | Aberdeen FC | - | Hibernian FC | 2:2 | ||||
| 10. Ronde | 16.10.1999 | Motherwell FC | - | Hibernian FC | 2:2 | ||||
| 11. Ronde | 23.10.1999 | Hibernian FC | - | Dundee FC | 5:2 | ||||
| 12. Ronde | 31.10.1999 | Hibernian FC | - | Dundee United | 3:2 | ||||
| 13. Ronde | 06.11.1999 | Kilmarnock FC | - | Hibernian FC | 0:2 |  |
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| 14. Ronde | 20.11.1999 | Rangers FC | - | Hibernian FC | 2:0 | ||||
| 15. Ronde | 24.11.1999 | Hibernian FC | - | St. Johnstone FC | 0:1 |
Schotland