| 2. Ronde | 07.08.1999 | Heart of Midlothian | - | Rangers FC | 0:4 |  |
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| 3. Ronde | 15.08.1999 | Rangers FC | - | Motherwell FC | 4:1 | |
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| 4. Ronde | 21.08.1999 | Rangers FC | - | Dundee United | 4:1 | ||||
| 5. Ronde | 28.08.1999 | Hibernian FC | - | Rangers FC | 0:1 |  |
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| 6. Ronde | 11.09.1999 | Rangers FC | - | Aberdeen FC | 3:0 | |
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| 8. Ronde | 25.09.1999 | Rangers FC | - | St. Johnstone FC | 3:1 | |
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| 9. Ronde | 02.10.1999 | Dundee FC | - | Rangers FC | 2:3 | |
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| 10. Ronde | 16.10.1999 | Kilmarnock FC | - | Rangers FC | 1:1 | ||||
| 12. Ronde | 30.10.1999 | Aberdeen FC | - | Rangers FC | 1:5 | |
Nederland
Indonesië 
