1. Round | 07/08/1999 | Leeds United | - | Derby County | 0:0 | ||||
2. Round | 10/08/1999 | Derby County | - | Arsenal FC | 1:2 | ||||
3. Round | 14/08/1999 | Derby County | - | Middlesbrough FC | 1:3 | ||||
4. Round | 21/08/1999 | Coventry City | - | Derby County | 2:0 | ||||
5. Round | 25/08/1999 | Sheffield Wednesday | - | Derby County | 0:2 | ||||
7. Round | 11/09/1999 | Wimbledon FC | - | Derby County | 2:2 | ||||
8. Round | 18/09/1999 | Derby County | - | Sunderland AFC | 0:5 | ||||
10. Round | 04/10/1999 | Southampton FC | - | Derby County | 3:3 | ||||
11. Round | 16/10/1999 | Derby County | - | Tottenham Hotspur | 0:1 | ||||
12. Round | 25/10/1999 | Newcastle United | - | Derby County | 2:0 | ||||
20. Round | 28/12/1999 | West Ham United | - | Derby County | 1:1 |