5. Round | 25/08/1999 | Sheffield Wednesday | - | Derby County | 0:2 | ||||
6. Round | 28/08/1999 | Derby County | - | Everton FC | 1:0 | ||||
7. Round | 11/09/1999 | Wimbledon FC | - | Derby County | 2:2 | ||||
8. Round | 18/09/1999 | Derby County | - | Sunderland AFC | 0:5 | ||||
9. Round | 25/09/1999 | Derby County | - | Bradford City | 0:1 | ||||
10. Round | 04/10/1999 | Southampton FC | - | Derby County | 3:3 | ||||
13. Round | 30/10/1999 | Derby County | - | Chelsea FC | 3:1 | ||||
14. Round | 06/11/1999 | Liverpool FC | - | Derby County | 2:0 |