| Hibernian FC v Heart Of Midlothian (Hearts) 14/08/1999 | View match | |
| Clyde v Hibernian FC 17/08/1999 | View match | |
| St Johnstone FC v Hibernian FC 21/08/1999 | View match | |
| Hibernian FC v Rangers (Glasgow) FC 28/08/1999 | View match | |
| Dundee United FC v Hibernian FC 11/09/1999 | View match | |
| Hibernian FC v Kilmarnock FC 19/09/1999 | View match | |
| Hibernian FC v Celtic (Glasgow) FC 25/09/1999 | View match | |
| Aberdeen FC v Hibernian FC 02/10/1999 | View match | |
| Kilmarnock FC v Hibernian FC 12/10/1999 | View match | |
| Motherwell FC v Hibernian FC 16/10/1999 | View match | |
| Hibernian FC v Dundee 23/10/1999 | View match | |
| Hibernian FC v Dundee United FC 31/10/1999 | View match |