1. Round | 07/08/1999 | Watford FC | - | Wimbledon FC | 2:3 | ||||
8. Round | 18/09/1999 | Manchester United | - | Wimbledon FC | 1:1 | ||||
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 | ||||
37. Round | 06/05/2000 | Wimbledon FC | - | Aston Villa | 2:2 | ||||
38. Round | 14/05/2000 | Southampton FC | - | Wimbledon FC | 2:0 |