The rams proved to be a major force in the premiership during the 1998 – 1999 season as they enjoyed their finest season in years, enjoying a great eighth position finish in the premier league. They were unfortunate to crash out of the FA cup in the quarter finals as they suffered a 1-0 defeat against Arsenal in the last eight. The following year saw the club reach the fourth round of the competition; however they suffered defeat against Burnley in the cup competition. They were not as much of a major force in the premiership as they finished it off in a disappointing 16th position.
The 2000 – 2001 season saw the club involved in relegation scrap, however they fortunately escaped demotion with a 17th position finish. They suffered defeats against Fulham in the fourth round of the league cup and in the same round, suffered defeat against Blackburn Rovers in the FA cup.
John Gregory was manager at Derby County during the 2001 – 2002 season and even he could not reverse Derby’s premiership fortunes as they finished the season off in 19th position, in turn suffering relegation into o the first division. They suffered embarrassment in the third round of the FA cup as they suffered defeat against lower league opposition, Bristol Rovers.