| 3. Round | 21/08/1998 | Heart of Midlothian | - | Aberdeen FC | 2:0 | ||||
| 4. Round | 29/08/1998 | Kilmarnock FC | - | Heart of Midlothian | 3:0 | ||||
| 5. Round | 11/09/1998 | Heart of Midlothian | - | Dundee FC | 0:2 |  |
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| 17. Round | 05/12/1998 | Heart of Midlothian | - | Celtic FC | 2:1 | ||||
| 18. Round | 11/12/1998 | Aberdeen FC | - | Heart of Midlothian | 2:0 | ||||
| 20. Round | 25/12/1998 | Kilmarnock FC | - | Heart of Midlothian | 1:0 |
Scotland