 |
 |
| ScPS | 02.01.1999 | Dundee FC | - | Dundee United | 1:3 | 11.751 |
| ScPS | 27.01.1999 | Dundee FC | - | Rangers FC | 0:4 | 9.453 |
| ScPS | 06.02.1999 | Dundee FC | - | Motherwell FC | 1:0 | 4.187 |
| ScPS | 27.02.1999 | Dundee FC | - | St. Johnstone FC | 0:1 | 7.245 |
| ScPS | 20.03.1999 | Dundee FC | - | Heart of Midlothian | 2:0 | 6.612 |
| ScPS | 18.04.1999 | Dundee FC | - | Rangers FC | 1:1 | 11.051 |
| ScPS | 24.04.1999 | Dundee FC | - | Kilmarnock FC | 2:1 | 4.296 |
| ScPS | 15.05.1999 | Dundee FC | - | Dunfermline Athletic | 3:1 | 4.179 |
| ScPS | 08.08.1999 | Dundee FC | - | Hibernian FC | 3:4 | 6.050 |
| ScPS | 21.08.1999 | Dundee FC | - | Celtic FC | 1:2 | 10.531 |
| ScPS | 19.09.1999 | Dundee FC | - | St. Johnstone FC | 1:2 | 5.283 |
| ScPS | 02.10.1999 | Dundee FC | - | Rangers FC | 2:3 | 10.494 |
| ScPS | 17.10.1999 | Dundee FC | - | Dundee United | 0:2 | 9.484 |
| ScPS | 30.10.1999 | Dundee FC | - | Heart of Midlothian | 1:0 | 6.018 |
| ScPS | 20.11.1999 | Dundee FC | - | Motherwell FC | 0:1 | 4.340 |
| ScPS | 27.12.1999 | Dundee FC | - | St. Johnstone FC | 1:1 | 6.232 |
Schottland