| 22. Round | 29/01/1999 | Heart of Midlothian | - | Motherwell FC | 0:2 | ||||
| 23. Round | 05/02/1999 | Dundee FC | - | Motherwell FC | 1:0 | ||||
| 25. Round | 26/02/1999 | Motherwell FC | - | Dunfermline Athletic | 1:1 | ||||
| 27. Round | 12/03/1999 | Rangers FC | - | Motherwell FC | 2:1 | ||||
| 28. Round | 19/03/1999 | Motherwell FC | - | Aberdeen FC | 1:1 | ||||
| 29. Round | 02/04/1999 | Dundee United | - | Motherwell FC | 0:3 | ||||
| 30. Round | 09/04/1999 | Motherwell FC | - | Dundee FC | 1:2 | ||||
| 31. Round | 16/04/1999 | Celtic FC | - | Motherwell FC | 1:0 | ||||
| 32. Round | 23/04/1999 | Motherwell FC | - | Heart of Midlothian | 0:4 | ||||
| 33. Round | 30/04/1999 | Kilmarnock FC | - | Motherwell FC | 0:1 | ||||
| 34. Round | 07/05/1999 | St. Johnstone FC | - | Motherwell FC | 0:0 | ||||
| 35. Round | 14/05/1999 | Motherwell FC | - | Rangers FC | 1:5 | ||||
| 36. Round | 22/05/1999 | Dunfermline Athletic | - | Motherwell FC | 1:2 |
Scotland
