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 | ||||
5. Round | 25/08/1999 | Everton FC | - | Wimbledon FC | 4:0 | ||||
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 | ||||
15. Round | 20/11/1999 | Leicester City | - | Wimbledon FC | 2:1 | ||||
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 | ||||
36. Round | 30/04/2000 | Bradford City | - | Wimbledon FC | 3:0 | ||||
37. Round | 06/05/2000 | Wimbledon FC | - | Aston Villa | 2:2 | ||||
38. Round | 14/05/2000 | Southampton FC | - | Wimbledon FC | 2:0 |