1. Round | 30/07/1999 | Hibernian FC | - | Motherwell FC | 2:2 | ||||
2. Round | 07/08/1999 | Dundee FC | - | Hibernian FC | 3:4 | ||||
3. Round | 13/08/1999 | Hibernian FC | - | Heart of Midlothian | 1:1 | ||||
8. Round | 24/09/1999 | Hibernian FC | - | Celtic FC | 0:2 | ||||
21. Round | 21/01/2000 | Dundee United | - | Hibernian FC | 0:0 | ||||
23. Round | 21/02/2000 | St. Johnstone FC | - | Hibernian FC | 1:0 | ||||
31. Round | 14/04/2000 | Hibernian FC | - | St. Johnstone FC | 3:3 | ||||
32. Round | 21/04/2000 | Celtic FC | - | Hibernian FC | 1:1 | ||||
34. Round | 05/05/2000 | Motherwell FC | - | Hibernian FC | 2:0 | ||||
36. Round | 20/05/2000 | Heart of Midlothian | - | Hibernian FC | 2:1 |