John Hollins took charge at Chelsea FC at the start of the 1985 -86 season and the club were emphatic in the top flight during his first year in charge, finishing the campaign in a strong sixth position. They also enjoyed a decent run in the League cup, meeting QPR in the quarter final, suffering a 20 defeat.
The 1986 -87 season did not run as smoothly for the Blues as they slid down the league table to finish off in 14th place. They reached the fourth round of the FA Cup; however they suffered a narrow 1-0 defeat against Watford. Steve Clarke signed for Chelsea in January 1987 from Scottish football club, St Mirren.
The 1987 – 88 season proved to be a debacle for Chelsea as they were very poor in the league, finishing the campaign off in an unacceptable 18th position, which in turn resulted in relegation for the club, in to the second division. Pat Nevin left Chelsea for Everton in July 1988 for a record transfer fee at the time of £925,000.
Bobby Campbell was installed as the new manager of the Blues during the 1988 -89 season and they were emphatic in the second division, finishing the campaign off at the top of the tier, gaining a staggering 99 points in the process. Dave Beasant had recently signed for the Blues and was outstanding in goal for them. They reached the fourth round of the FA Cup, suffering defeat against Barnsley.
Chelsea were outstanding in their season back in the top flight, finishing it off in an impressive fifth place, establishing themselves in the top flight. The Blues lost to Bristol City in the fourth round of the FA Cup.
The Chelsea side of the 1989 – 90 season included, Steve Clarke, Tony Dorigo, John Bumstead, David Lee, Ken Monkou, Kevin McAllister, Peter Nicholas, Kerry Dixon, Gordon Durie and Kevin Wilson.