| 1. Round | 30/07/1999 | Hibernian FC | - | Motherwell FC | 2:2 | ||||
| 2. Round | 06/08/1999 | Motherwell FC | - | Dundee United | 2:2 | ||||
| 3. Round | 14/08/1999 | Rangers FC | - | Motherwell FC | 4:1 | ||||
| 4. Round | 20/08/1999 | Kilmarnock FC | - | Motherwell FC | 0:1 | ||||
| 5. Round | 27/08/1999 | Motherwell FC | - | Dundee FC | 0:2 | ||||
| 6. Round | 10/09/1999 | St. Johnstone FC | - | Motherwell FC | 1:1 | ||||
| 10. Round | 15/10/1999 | Motherwell FC | - | Hibernian FC | 2:2 | ||||
| 8. Round | 19/10/1999 | Motherwell FC | - | Aberdeen FC | 5:6 |  |
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| 11. Round | 22/10/1999 | Dundee United | - | Motherwell FC | 0:2 | |
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| 9. Round | 26/10/1999 | Celtic FC | - | Motherwell FC | 0:1 |  |
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| 13. Round | 05/11/1999 | Heart of Midlothian | - | Motherwell FC | 1:1 | ||||
| 14. Round | 19/11/1999 | Dundee FC | - | Motherwell FC | 0:1 | ||||
| 7. Round | 22/11/1999 | Motherwell FC | - | Heart of Midlothian | 2:1 | ||||
| 16. Round | 27/11/1999 | Motherwell FC | - | Celtic FC | 3:2 | ||||
| 18. Round | 10/12/1999 | Hibernian FC | - | Motherwell FC | 2:2 | ||||
| 19. Round | 17/12/1999 | Motherwell FC | - | Rangers FC | 1:5 |
England