| Airdrieonians (Old) v Hibernian FC 30/01/1999 | View match | |
| Stirling Albion FC v Hibernian FC 02/02/1999 | View match | |
| Hibernian FC v Stranraer 06/02/1999 | View match | |
| Falkirk FC v Hibernian FC 20/02/1999 | View match | |
| 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 |