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 | ||||
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 | ||||
17. Round | 04/12/1999 | Wimbledon FC | - | Watford FC | 5:0 | ||||
18. Round | 18/12/1999 | Arsenal FC | - | Wimbledon FC | 1:1 | ||||
36. Round | 30/04/2000 | Bradford City | - | Wimbledon FC | 3:0 | ||||
37. Round | 06/05/2000 | Wimbledon FC | - | Aston Villa | 2:2 |