7. Round | 22/11/1999 | Motherwell FC | - | Heart of Midlothian | 2:1 | ||||
16. Round | 26/11/1999 | Kilmarnock FC | - | Heart of Midlothian | 2:2 | ||||
17. Round | 04/12/1999 | Heart of Midlothian | - | Dundee United | 3:0 | ||||
15. Round | 07/12/1999 | Aberdeen FC | - | Heart of Midlothian | 3:1 | ||||
23. Round | 21/03/2000 | Heart of Midlothian | - | Aberdeen FC | 3:0 |