Coventry City finished the 1985 – 1986 season once again towards the foot at the table in 17th position as it proved to be the last campaign that saw Don Mackay in charge at the club. George Curtis took charge at the club during the 1986 – 1987 campaign and his Coventry City side finished doff the season in a much improved 10th position finish, their highest finish since 1979. They enjoyed a terrific run in the FA cup that saw them reach the final of the cup competition where they met Tottenham Hotspur in the final. Don Hutchinson scored in the final and they scored a goal from an own goal by Gary Mabbutt.
Their great FA Cup run boosted their form in the top flight over the next several years as they were in emphatic form in the league as they finished off their campaigns in tenth, twelfth and seventh positions respectively. John Sillett took charge at the club between 1987 and 1990. The sky blues enjoyed a fantastic run in the league cup during the 1989 – 1990 season as they met Nottingham forest in the last four of the competition, suffering a 2-1 defeat on aggregate to the eventual cup winners in the semi finals.
The 1989 – 1990 Coventry city team included players like, Steve Ogrizovic, Brain Burrows, Tony Dobson, Mickey Gynn, Peter Billing, Trevor Peake, Kevin Gallacher, David Speedie, Cyrille Regis. Kevin Drinkell and David Smith.