1. Round 30/07/1999 Hibernian FC - Motherwell FC 2:2
2. Round 06/08/1999 Motherwell FC - Dundee United 2:2
3. Round 14/08/1999 Rangers FC - Motherwell FC 4:1
5. Round 27/08/1999 Motherwell FC - Dundee FC 0:2
6. Round 10/09/1999 St. Johnstone FC - Motherwell FC 1:1
10. Round 15/10/1999 Motherwell FC - Hibernian FC 2:2
8. Round 19/10/1999 Motherwell FC - Aberdeen FC 5:6
11. Round 22/10/1999 Dundee United - Motherwell FC 0:2 yellow card
9. Round 26/10/1999 Celtic FC - Motherwell FC 0:1
12. Round 29/10/1999 Motherwell FC - St. Johnstone FC 1:0
13. Round 05/11/1999 Heart of Midlothian - Motherwell FC 1:1
14. Round 19/11/1999 Dundee FC - Motherwell FC 0:1
7. Round 22/11/1999 Motherwell FC - Heart of Midlothian 2:1
16. Round 27/11/1999 Motherwell FC - Celtic FC 3:2
18. Round 10/12/1999 Hibernian FC - Motherwell FC 2:2 yellow card
19. Round 17/12/1999 Motherwell FC - Rangers FC 1:5
21. Round 21/01/2000 St. Johnstone FC - Motherwell FC 1:1 yellow card
17. Round 25/01/2000 Aberdeen FC - Motherwell FC 1:1
22. Round 04/02/2000 Motherwell FC - Dundee FC 0:3
23. Round 11/02/2000 Kilmarnock FC - Motherwell FC 0:2
15. Round 21/02/2000 Motherwell FC - Kilmarnock FC 0:4
20. Round 29/02/2000 Motherwell FC - Heart of Midlothian 0:2
25. Round 03/03/2000 Motherwell FC - Aberdeen FC 1:0
27. Round 17/03/2000 Rangers FC - Motherwell FC 6:2
28. Round 24/03/2000 Heart of Midlothian - Motherwell FC 0:0
29. Round 31/03/2000 Motherwell FC - St. Johnstone FC 2:1
31. Round 15/04/2000 Motherwell FC - Kilmarnock FC 2:0
26. Round 18/04/2000 Motherwell FC - Dundee United 1:3
32. Round 21/04/2000 Aberdeen FC - Motherwell FC 2:1
36. Round 20/05/2000 Motherwell FC - Rangers FC 2:0