1. Round | 30/07/1999 | St. Johnstone FC | - | Heart of Midlothian | 1:4 | ||||
2. Round | 06/08/1999 | Celtic FC | - | St. Johnstone FC | 3:0 | ||||
3. Round | 14/08/1999 | St. Johnstone FC | - | Kilmarnock FC | 2:0 | ||||
4. Round | 20/08/1999 | St. Johnstone FC | - | Hibernian FC | 1:1 | ||||
5. Round | 28/08/1999 | Aberdeen FC | - | St. Johnstone FC | 0:3 | ||||
6. Round | 10/09/1999 | St. Johnstone FC | - | Motherwell FC | 1:1 | ||||
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 | ||||
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 | ||||
15. Round | 23/11/1999 | Hibernian FC | - | St. Johnstone FC | 0:1 | ||||
16. Round | 26/11/1999 | Dundee United | - | St. Johnstone FC | 1:0 |