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 | ||||
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 | ||||
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 | ||||
17. Round | 04/12/1999 | Wimbledon FC | - | Watford FC | 5:0 | ||||
18. Round | 18/12/1999 | Arsenal FC | - | Wimbledon FC | 1:1 | ||||
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 |