| 13. Round | 16/11/1998 | Nottingham Forest | - | Derby County | 2:2 | ||||
| 14. Round | 22/11/1998 | Derby County | - | West Ham United | 0:2 | ||||
| 15. Round | 28/11/1998 | Southampton FC | - | Derby County | 0:1 | ||||
| 16. Round | 05/12/1998 | Derby County | - | Arsenal FC | 0:0 | ||||
| 17. Round | 12/12/1998 | Derby County | - | Chelsea FC | 2:2 | ||||
| 18. Round | 19/12/1998 | Coventry City | - | Derby County | 1:1 | ||||
| 19. Round | 26/12/1998 | Everton FC | - | Derby County | 0:0 | ||||
| 20. Round | 28/12/1998 | Derby County | - | Middlesbrough FC | 2:1 | ||||
| 21. Round | 09/01/1999 | Wimbledon FC | - | Derby County | 2:1 | ||||
| 22. Round | 16/01/1999 | Derby County | - | Blackburn Rovers | 1:0 | ||||
| 30. Round | 20/03/1999 | Leeds United | - | Derby County | 4:1 | ||||
| 33. Round | 10/04/1999 | Derby County | - | Nottingham Forest | 1:0 | ||||
| 35. Round | 24/04/1999 | Derby County | - | Southampton FC | 0:0 | ||||
| 36. Round | 02/05/1999 | Arsenal FC | - | Derby County | 1:0 | ||||
| 25. Round | 05/05/1999 | Leicester City | - | Derby County | 1:2 | ||||
| 37. Round | 08/05/1999 | Derby County | - | Coventry City | 0:0 | ||||
| 38. Round | 16/05/1999 | Chelsea FC | - | Derby County | 2:1 |
Estonia