| 5. Ronde | 25.08.1999 | Sheffield Wednesday | - | Derby County | 0:2 | ||||
| 6. Ronde | 28.08.1999 | Derby County | - | Everton FC | 1:0 | ||||
| 7. Ronde | 11.09.1999 | Wimbledon FC | - | Derby County | 2:2 | ||||
| 8. Ronde | 18.09.1999 | Derby County | - | Sunderland AFC | 0:5 | ||||
| 9. Ronde | 25.09.1999 | Derby County | - | Bradford City | 0:1 | ||||
| 10. Ronde | 04.10.1999 | Southampton FC | - | Derby County | 3:3 |  |
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| 11. Ronde | 16.10.1999 | Derby County | - | Tottenham Hotspur | 0:1 | ||||
| 12. Ronde | 25.10.1999 | Newcastle United | - | Derby County | 2:0 | ||||
| 13. Ronde | 30.10.1999 | Derby County | - | Chelsea FC | 3:1 | ||||
| 14. Ronde | 06.11.1999 | Liverpool FC | - | Derby County | 2:0 |
Engeland