| 1. Round | 31/07/1998 | Motherwell FC | - | St. Johnstone FC | 1:0 | ||||
| 2. Round | 14/08/1998 | Rangers FC | - | Motherwell FC | 2:1 | ||||
| 3. Round | 21/08/1998 | Motherwell FC | - | Dunfermline Athletic | 0:0 |  |
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| 4. Round | 29/08/1998 | Motherwell FC | - | Dundee United | 1:0 | ||||
| 5. Round | 11/09/1998 | Aberdeen FC | - | Motherwell FC | 1:1 | |
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| 6. Round | 18/09/1998 | Motherwell FC | - | Kilmarnock FC | 0:0 | |
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| 7. Round | 22/09/1998 | Heart of Midlothian | - | Motherwell FC | 3:0 | ||||
| 8. Round | 25/09/1998 | Dundee FC | - | Motherwell FC | 1:0 | ||||
| 9. Round | 02/10/1998 | Motherwell FC | - | Celtic FC | 1:2 | ||||
| 10. Round | 16/10/1998 | St. Johnstone FC | - | Motherwell FC | 5:0 | ||||
| 21. Round | 31/12/1998 | Motherwell FC | - | Kilmarnock FC | 1:2 | |
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| 22. Round | 29/01/1999 | Heart of Midlothian | - | Motherwell FC | 0:2 | ||||
| 27. Round | 12/03/1999 | Rangers FC | - | Motherwell FC | 2:1 | ||||
| 32. Round | 23/04/1999 | Motherwell FC | - | Heart of Midlothian | 0:4 | ||||
| 33. Round | 30/04/1999 | Kilmarnock FC | - | Motherwell FC | 0:1 | |
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| 34. Round | 07/05/1999 | St. Johnstone FC | - | Motherwell FC | 0:0 | ||||
| 36. Round | 22/05/1999 | Dunfermline Athletic | - | Motherwell FC | 1:2 | |
Netherlands