| 1. Jornada | 31.07.1999 | Rangers FC | - | Kilmarnock FC | 2:1 |  |
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| 2. Jornada | 07.08.1999 | Heart of Midlothian | - | Rangers FC | 0:4 | ||||
| 6. Jornada | 11.09.1999 | Rangers FC | - | Aberdeen FC | 3:0 | ||||
| 9. Jornada | 02.10.1999 | Dundee FC | - | Rangers FC | 2:3 |  |
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| 12. Jornada | 30.10.1999 | Aberdeen FC | - | Rangers FC | 1:5 | |
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| 13. Jornada | 07.11.1999 | Rangers FC | - | Celtic FC | 4:2 | |
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| 14. Jornada | 20.11.1999 | Rangers FC | - | Hibernian FC | 2:0 | ||||
| 20. Jornada | 27.12.1999 | Celtic FC | - | Rangers FC | 1:1 |
Argentina