6. Round | 10/09/1999 | St. Johnstone FC | - | Motherwell FC | 1:1 | ||||
7. Round | 18/09/1999 | Dundee FC | - | St. Johnstone FC | 1:2 | ||||
10. Round | 15/10/1999 | Heart of Midlothian | - | St. Johnstone FC | 1:1 | ||||
11. Round | 23/10/1999 | St. Johnstone FC | - | Celtic FC | 1:2 | ||||
9. Round | 26/10/1999 | St. Johnstone FC | - | Dundee United | 0:1 | ||||
12. Round | 29/10/1999 | Motherwell FC | - | St. Johnstone FC | 1:0 | ||||
13. Round | 05/11/1999 | St. Johnstone FC | - | Dundee FC | 0:1 |