| 1. Round | 31/07/1998 | Motherwell FC | - | St. Johnstone FC | 1:0 | ||||
| 3. Round | 22/08/1998 | Dundee FC | - | St. Johnstone FC | 0:1 |  |
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| 4. Round | 28/08/1998 | Rangers FC | - | St. Johnstone FC | 4:0 | ||||
| 5. Round | 11/09/1998 | St. Johnstone FC | - | Dunfermline Athletic | 1:1 | ||||
| 9. Round | 03/10/1998 | Heart of Midlothian | - | St. Johnstone FC | 1:1 | ||||
| 14. Round | 13/11/1998 | St. Johnstone FC | - | Celtic FC | 2:1 | ||||
| 15. Round | 20/11/1998 | Aberdeen FC | - | St. Johnstone FC | 0:1 | ||||
| 17. Round | 04/12/1998 | Dundee United | - | St. Johnstone FC | 1:1 | ||||
| 16. Round | 08/12/1998 | St. Johnstone FC | - | Heart of Midlothian | 1:1 | ||||
| 18. Round | 11/12/1998 | St. Johnstone FC | - | Dundee FC | 1:1 | ||||
| 21. Round | 01/01/1999 | St. Johnstone FC | - | Aberdeen FC | 4:1 | ||||
| 22. Round | 30/01/1999 | Celtic FC | - | St. Johnstone FC | 5:0 | ||||
| 23. Round | 05/02/1999 | St. Johnstone FC | - | Dundee United | 1:0 | ||||
| 24. Round | 19/02/1999 | Heart of Midlothian | - | St. Johnstone FC | 0:2 | |
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| 25. Round | 26/02/1999 | Dundee FC | - | St. Johnstone FC | 0:1 | ||||
| 27. Round | 12/03/1999 | St. Johnstone FC | - | Kilmarnock FC | 0:1 |
Scotland