2. Round | 10/08/1999 | Wimbledon FC | - | Middlesbrough FC | 2:3 | ||||
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 | ||||
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 | ||||
16. Round | 27/11/1999 | Middlesbrough FC | - | Wimbledon FC | 0:0 | ||||
19. Round | 26/12/1999 | Wimbledon FC | - | West Ham United | 2:2 | ||||
20. Round | 28/12/1999 | Liverpool FC | - | Wimbledon FC | 3:1 | ||||
23. Round | 22/01/2000 | Wimbledon FC | - | Newcastle United | 2:0 | ||||
24. Round | 06/02/2000 | Wimbledon FC | - | Everton FC | 0:3 | ||||
30. Round | 26/03/2000 | West Ham United | - | Wimbledon FC | 2:1 | ||||
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 |