The 1980 – 1981 season was the last one that saw Bob Dennison in charge at the club as his side finished the campaign off in 16th position and reached the fifth round of the FA Cup as they suffered defeat in the last sixteen against Tottenham Hotspur. Dennison led Coventry in to their finest ever league cup campaign as they raced in to the semi finals, however lost 4-3 on aggregate against West Ham United in the last four of the competition.
Dave Sexton took charge at the club in 1981 and went on to spend two years in charge at the club. he guided City to a 14th position finish at the end of the 1981 – 1982 season, however he saw his Coventry side involved in  relegation battle during the 1982 – 1983 campaigns they avoided the drop with a 19th place finish.
Bobby Gould took charge at the club in 1983, however he could not improve their ranking in the top flight as they once again narrowly escaped relegation with a 19th place finish. They reached the fourth round of the FA cup, suffering defeat against Sheffield Wednesday in the competition. The 1984 – 1985 season saw the arrival of Don Mackay during the campaign as the sky blues finished off in 18th position. They reached the second round of the league cup, suffering defeat against Walsall. They purchased Cyrille Regis in the summer of 1984 and he proved to be a great signing for the club.