| Ayr United FC v Hibernian FC 27/02/1999 | View match | |
| Clydebank FC (Old) v Hibernian FC 13/03/1999 | View match | |
| Hibernian FC v Airdrie United FC 20/03/1999 | View match | |
| Hamilton Academicals v Hibernian FC 03/04/1999 | View match | |
| Raith Rovers FC v Hibernian FC 10/04/1999 | View match | |
| Hibernian FC v St Mirren FC 17/04/1999 | View match | |
| Hibernian FC v Morton FC 24/04/1999 | View match | |
| Stranraer v Hibernian FC 01/05/1999 | View match | |
| Hibernian FC v Falkirk FC 08/05/1999 | View match | |
| Whitley Bay v Hibernian FC 24/07/1999 | View match | |
| Hibernian FC v Motherwell FC 31/07/1999 | View match | |
| Dundee v Hibernian FC 08/08/1999 | View match |