| Dundee v Ayr United FC 29/01/2000 | View match | |
| Motherwell FC v Dundee 05/02/2000 | View match | |
| Dundee v Celtic (Glasgow) FC 12/02/2000 | View match | |
| Ayr United FC v Dundee 15/02/2000 | View match | |
| Dundee v Aberdeen FC 23/02/2000 | View match | |
| Dundee v Rangers (Glasgow) FC 27/02/2000 | View match | |
| Celtic (Glasgow) FC v Dundee 01/03/2000 | View match | |
| Kilmarnock FC v Dundee 04/03/2000 | View match | |
| Hibernian FC v Dundee 21/03/2000 | View match | |
| St Johnstone FC v Dundee 25/03/2000 | View match | |
| Dundee v Heart Of Midlothian (Hearts) 01/04/2000 | View match | |
| Dundee v Motherwell FC 08/04/2000 | View match |