12. Round | 23/10/1999 | Aston Villa | - | Wimbledon FC | 1:1 | ||||
17. Round | 04/12/1999 | Wimbledon FC | - | Watford FC | 5:0 | ||||
18. Round | 18/12/1999 | Arsenal FC | - | Wimbledon FC | 1:1 | ||||
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 | ||||
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 | ||||
28. Round | 11/03/2000 | Wimbledon FC | - | Leicester City | 2:1 | ||||
31. Round | 01/04/2000 | Wimbledon FC | - | Arsenal FC | 1:3 | ||||
33. Round | 16/04/2000 | Wimbledon FC | - | Liverpool FC | 1:2 | ||||
34. Round | 22/04/2000 | Tottenham Hotspur | - | Wimbledon FC | 2:0 |