| 25. Round | 26/02/1999 | Motherwell FC | - | Dunfermline Athletic | 1:1 | ||||
| 27. Round | 12/03/1999 | Dunfermline Athletic | - | Dundee FC | 2:0 |  |
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| 28. Round | 19/03/1999 | Dunfermline Athletic | - | St. Johnstone FC | 1:0 | ||||
| 29. Round | 02/04/1999 | Aberdeen FC | - | Dunfermline Athletic | 3:1 | ||||
| 30. Round | 13/04/1999 | Rangers FC | - | Dunfermline Athletic | 1:0 | ||||
| 31. Round | 16/04/1999 | Dunfermline Athletic | - | Kilmarnock FC | 0:6 | ||||
| 32. Round | 23/04/1999 | Dunfermline Athletic | - | Dundee United | 2:2 | ||||
| 33. Round | 02/05/1999 | Heart of Midlothian | - | Dunfermline Athletic | 2:0 | ||||
| 34. Round | 07/05/1999 | Dunfermline Athletic | - | Celtic FC | 1:2 |
Scotland