1. Round 08/08/1999 Manchester City - Wolverhampton Wanderers 0:1
2. Round 14/08/1999 Wolverhampton Wanderers - Portsmouth FC 1:1
3. Round 21/08/1999 Queens Park Rangers - Wolverhampton Wanderers 1:1
4. Round 28/08/1999 Wolverhampton Wanderers - Walsall FC 1:2
7. Round 11/09/1999 Wolverhampton Wanderers - Huddersfield Town 0:1
8. Round 19/09/1999 Nottingham Forest - Wolverhampton Wanderers 1:1 yellow card
9. Round 25/09/1999 Sheffield United - Wolverhampton Wanderers 3:0 yellow card
5. Round 28/09/1999 Crystal Palace - Wolverhampton Wanderers 1:1 yellow card
10. Round 03/10/1999 Wolverhampton Wanderers - West Bromwich Albion 1:1
11. Round 09/10/1999 Wolverhampton Wanderers - Bolton Wanderers 1:0
12. Round 16/10/1999 Barnsley FC - Wolverhampton Wanderers 1:2
13. Round 19/10/1999 Fulham FC - Wolverhampton Wanderers 0:1 yellow card
14. Round 23/10/1999 Wolverhampton Wanderers - Port Vale FC 2:2 yellow card
15. Round 26/10/1999 Wolverhampton Wanderers - Sheffield United 1:0
16. Round 31/10/1999 West Bromwich Albion - Wolverhampton Wanderers 1:1
19. Round 20/11/1999 Wolverhampton Wanderers - Swindon Town 1:1
20. Round 24/11/1999 Ipswich Town - Wolverhampton Wanderers 1:0
21. Round 27/11/1999 Tranmere Rovers - Wolverhampton Wanderers 1:0 yellow card
22. Round 03/12/1999 Wolverhampton Wanderers - Manchester City 4:1 Goal
18. Round 14/12/1999 Crewe Alexandra - Wolverhampton Wanderers 1:0
23. Round 17/12/1999 Wolverhampton Wanderers - Birmingham City 2:1
24. Round 26/12/1999 Stockport County - Wolverhampton Wanderers 3:2 yellow card
25. Round 28/12/1999 Wolverhampton Wanderers - Norwich City 1:0
26. Round 03/01/2000 Blackburn Rovers - Wolverhampton Wanderers 1:1 red card
6. Round 11/01/2000 Wolverhampton Wanderers - Charlton Athletic 2:3
27. Round 15/01/2000 Portsmouth FC - Wolverhampton Wanderers 2:3
28. Round 22/01/2000 Wolverhampton Wanderers - Queens Park Rangers 3:2
29. Round 29/01/2000 Walsall FC - Wolverhampton Wanderers 1:1
30. Round 05/02/2000 Wolverhampton Wanderers - Crystal Palace 2:1
31. Round 12/02/2000 Charlton Athletic - Wolverhampton Wanderers 2:0
32. Round 16/02/2000 Wolverhampton Wanderers - Tranmere Rovers 4:0 yellow card
33. Round 26/02/2000 Wolverhampton Wanderers - Nottingham Forest 3:0
34. Round 04/03/2000 Huddersfield Town - Wolverhampton Wanderers 2:0
35. Round 07/03/2000 Grimsby Town - Wolverhampton Wanderers 1:0
36. Round 11/03/2000 Wolverhampton Wanderers - Ipswich Town 2:1
37. Round 18/03/2000 Swindon Town - Wolverhampton Wanderers 1:2 Goal
38. Round 21/03/2000 Wolverhampton Wanderers - Crewe Alexandra 2:0
39. Round 25/03/2000 Wolverhampton Wanderers - Stockport County 2:2
40. Round 01/04/2000 Birmingham City - Wolverhampton Wanderers 1:0
41. Round 08/04/2000 Wolverhampton Wanderers - Blackburn Rovers 2:1 Goal
42. Round 15/04/2000 Norwich City - Wolverhampton Wanderers 1:0
43. Round 22/04/2000 Wolverhampton Wanderers - Barnsley FC 2:0
45. Round 30/04/2000 Wolverhampton Wanderers - Fulham FC 3:0 Goal
44. Round 03/05/2000 Bolton Wanderers - Wolverhampton Wanderers 2:1
46. Round 07/05/2000 Port Vale FC - Wolverhampton Wanderers 0:1