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