| 4. Round | 20/08/1999 | St. Johnstone FC | - | Hibernian FC | 1:1 | ||||
| 5. Round | 28/08/1999 | Aberdeen FC | - | St. Johnstone FC | 0:3 |  |
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| 6. Round | 10/09/1999 | St. Johnstone FC | - | Motherwell FC | 1:1 | |
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| 7. Round | 18/09/1999 | Dundee FC | - | St. Johnstone FC | 1:2 | ||||
| 8. Round | 24/09/1999 | Rangers FC | - | St. Johnstone FC | 3:1 | ||||
| 10. Round | 15/10/1999 | Heart of Midlothian | - | St. Johnstone FC | 1:1 | ||||
| 12. Round | 29/10/1999 | Motherwell FC | - | St. Johnstone FC | 1:0 | ||||
| 16. Round | 26/11/1999 | Dundee United | - | St. Johnstone FC | 1:0 | ||||
| 33. Round | 28/04/2000 | Dundee United | - | St. Johnstone FC | 0:1 | ||||
| 34. Round | 05/05/2000 | Heart of Midlothian | - | St. Johnstone FC | 0:0 |
Scotland