| 1. Ronde | 31.07.1999 | St. Johnstone FC | - | Heart of Midlothian | 1:4 | ||||
| 2. Ronde | 07.08.1999 | Celtic FC | - | St. Johnstone FC | 3:0 | ||||
| 3. Ronde | 15.08.1999 | St. Johnstone FC | - | Kilmarnock FC | 2:0 | ||||
| 4. Ronde | 21.08.1999 | St. Johnstone FC | - | Hibernian FC | 1:1 | ||||
| 5. Ronde | 29.08.1999 | Aberdeen FC | - | St. Johnstone FC | 0:3 | ||||
| 6. Ronde | 11.09.1999 | St. Johnstone FC | - | Motherwell FC | 1:1 | ||||
| 7. Ronde | 19.09.1999 | Dundee FC | - | St. Johnstone FC | 1:2 | ||||
| 8. Ronde | 25.09.1999 | Rangers FC | - | St. Johnstone FC | 3:1 |  |
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| 10. Ronde | 16.10.1999 | Heart of Midlothian | - | St. Johnstone FC | 1:1 | ||||
| 11. Ronde | 24.10.1999 | St. Johnstone FC | - | Celtic FC | 1:2 | ||||
| 12. Ronde | 30.10.1999 | Motherwell FC | - | St. Johnstone FC | 1:0 | ||||
| 13. Ronde | 06.11.1999 | St. Johnstone FC | - | Dundee FC | 0:1 | ||||
| 14. Ronde | 21.11.1999 | St. Johnstone FC | - | Aberdeen FC | 1:1 | ||||
| 15. Ronde | 24.11.1999 | Hibernian FC | - | St. Johnstone FC | 0:1 | ||||
| 16. Ronde | 27.11.1999 | Dundee United | - | St. Johnstone FC | 1:0 | ||||
| 21. Ronde | 22.01.2000 | St. Johnstone FC | - | Motherwell FC | 1:1 | ||||
| 22. Ronde | 05.02.2000 | Aberdeen FC | - | St. Johnstone FC | 2:1 |
Portugal