 |
 |
| ScPS | 01/01/1999 | Motherwell FC | - | Kilmarnock FC | 1:2 | 8.532 |
| ScPS | 21/02/1999 | Motherwell FC | - | Celtic FC | 1:7 | 11.963 |
| ScPS | 27/02/1999 | Motherwell FC | - | Dunfermline Athletic | 1:1 | 6.094 |
| ScPS | 20/03/1999 | Motherwell FC | - | Aberdeen FC | 1:1 | 6.963 |
| ScPS | 10/04/1999 | Motherwell FC | - | Dundee FC | 1:2 | 5.717 |
| ScPS | 24/04/1999 | Motherwell FC | - | Heart of Midlothian | 0:4 | 8.926 |
| ScPS | 15/05/1999 | Motherwell FC | - | Rangers FC | 1:5 | 11.078 |
| ScPS | 07/08/1999 | Motherwell FC | - | Dundee United | 2:2 | 6.791 |
| ScPS | 28/08/1999 | Motherwell FC | - | Dundee FC | 0:2 | 6.278 |
| ScPS | 16/10/1999 | Motherwell FC | - | Hibernian FC | 2:2 | 7.559 |
| ScPS | 20/10/1999 | Motherwell FC | - | Aberdeen FC | 5:6 | 5.009 |
| ScPS | 30/10/1999 | Motherwell FC | - | St. Johnstone FC | 1:0 | 6.172 |
| ScPS | 23/11/1999 | Motherwell FC | - | Heart of Midlothian | 2:1 | 7.850 |
| ScPS | 28/11/1999 | Motherwell FC | - | Celtic FC | 3:2 | 12.775 |
| ScPS | 18/12/1999 | Motherwell FC | - | Rangers FC | 1:5 | 13.102 |
Scotland