1. Round | 07/08/1999 | Middlesbrough FC | - | Bradford City | 0:1 | ||||
3. Round | 14/08/1999 | Bradford City | - | Sheffield Wednesday | 1:1 | ||||
4. Round | 21/08/1999 | Watford FC | - | Bradford City | 1:0 | ||||
5. Round | 25/08/1999 | Arsenal FC | - | Bradford City | 2:0 | ||||
6. Round | 28/08/1999 | Bradford City | - | West Ham United | 0:3 | ||||
7. Round | 12/09/1999 | Bradford City | - | Tottenham Hotspur | 1:1 | ||||
8. Round | 18/09/1999 | Aston Villa | - | Bradford City | 1:0 | ||||
9. Round | 25/09/1999 | Derby County | - | Bradford City | 0:1 | ||||
10. Round | 02/10/1999 | Bradford City | - | Sunderland AFC | 0:4 | ||||
11. Round | 16/10/1999 | Wimbledon FC | - | Bradford City | 3:2 | ||||
12. Round | 23/10/1999 | Bradford City | - | Leicester City | 3:1 |