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 | ||||
6. Round | 28/08/1999 | Derby County | - | Everton FC | 1:0 | ||||
9. Round | 25/09/1999 | Derby County | - | Bradford City | 0:1 | ||||
10. Round | 04/10/1999 | Southampton FC | - | Derby County | 3:3 | ||||
11. Round | 16/10/1999 | Derby County | - | Tottenham Hotspur | 0:1 | ||||
13. Round | 30/10/1999 | Derby County | - | Chelsea FC | 3:1 | ||||
14. Round | 06/11/1999 | Liverpool FC | - | Derby County | 2:0 | ||||
15. Round | 20/11/1999 | Derby County | - | Manchester United | 1:2 |