1. Round 07/08/1999 Watford FC - Wimbledon FC 2:3
2. Round 10/08/1999 Wimbledon FC - Middlesbrough FC 2:3
3. Round 14/08/1999 Wimbledon FC - Coventry City 1:1
4. Round 21/08/1999 Newcastle United - Wimbledon FC 3:3
5. Round 25/08/1999 Everton FC - Wimbledon FC 4:0
6. Round 28/08/1999 Wimbledon FC - Chelsea FC 0:1
7. Round 11/09/1999 Wimbledon FC - Derby County 2:2
8. Round 18/09/1999 Manchester United - Wimbledon FC 1:1
9. Round 26/09/1999 Wimbledon FC - Tottenham Hotspur 1:1
10. Round 02/10/1999 Sheffield Wednesday - Wimbledon FC 5:1
11. Round 16/10/1999 Wimbledon FC - Bradford City 3:2
12. Round 23/10/1999 Aston Villa - Wimbledon FC 1:1
13. Round 30/10/1999 Wimbledon FC - Southampton FC 1:1
14. Round 07/11/1999 Wimbledon FC - Leeds United 2:0
15. Round 20/11/1999 Leicester City - Wimbledon FC 2:1
16. Round 27/11/1999 Middlesbrough FC - Wimbledon FC 0:0
17. Round 04/12/1999 Wimbledon FC - Watford FC 5:0
18. Round 18/12/1999 Arsenal FC - Wimbledon FC 1:1
19. Round 26/12/1999 Wimbledon FC - West Ham United 2:2
20. Round 28/12/1999 Liverpool FC - Wimbledon FC 3:1
21. Round 03/01/2000 Wimbledon FC - Sunderland AFC 1:0
22. Round 15/01/2000 Coventry City - Wimbledon FC 2:0
23. Round 22/01/2000 Wimbledon FC - Newcastle United 2:0
24. Round 06/02/2000 Wimbledon FC - Everton FC 0:3
25. Round 12/02/2000 Chelsea FC - Wimbledon FC 3:1
26. Round 26/02/2000 Wimbledon FC - Manchester United 2:2
27. Round 04/03/2000 Derby County - Wimbledon FC 4:0
29. Round 19/03/2000 Leeds United - Wimbledon FC 4:1
30. Round 26/03/2000 West Ham United - Wimbledon FC 2:1
31. Round 01/04/2000 Wimbledon FC - Arsenal FC 1:3
32. Round 08/04/2000 Sunderland AFC - Wimbledon FC 2:1
35. Round 12/04/2000 Wimbledon FC - Sheffield Wednesday 0:2
33. Round 16/04/2000 Wimbledon FC - Liverpool FC 1:2
34. Round 22/04/2000 Tottenham Hotspur - Wimbledon FC 2:0
36. Round 30/04/2000 Bradford City - Wimbledon FC 3:0 yellow card
37. Round 06/05/2000 Wimbledon FC - Aston Villa 2:2
38. Round 14/05/2000 Southampton FC - Wimbledon FC 2:0