| Dundee v Kilmarnock FC 24/04/1999 | View match | |
| Aberdeen FC v Dundee 08/05/1999 | View match | |
| Dundee v Dunfermline Athletic 15/05/1999 | View match | |
| St Johnstone FC v Dundee 23/05/1999 | View match | |
| Dundee United FC v Dundee 31/07/1999 | View match | |
| Dundee v Hibernian FC 08/08/1999 | View match | |
| Aberdeen FC v Dundee 14/08/1999 | View match | |
| Dundee v Dumbarton 17/08/1999 | View match | |
| Dundee v Celtic (Glasgow) FC 21/08/1999 | View match | |
| Motherwell FC v Dundee 28/08/1999 | View match | |
| Heart Of Midlothian (Hearts) v Dundee 11/09/1999 | View match | |
| Dundee v St Johnstone FC 19/09/1999 | View match |