#4 Chelsea had 4 managers (and 1 interim manager) in 2 seasons
Chelsea are known for being extremely impatient with their managers and it was not demonstrated in a better way than during the period between 2007 and 2009. After Jose Mourinho left Stamford Bridge five games into the 2007-08 season, Chelsea appointed Israeli Avram Grant to take over the duties for the Blues.
He did a decent job, despite not being well liked, taking Chelsea to the Champions League final and battling for the Premier League title until the last day. Unfortunately, it was not enough and Grant was sacked at the end of the season. To solve their managerial problems Chelsea went big, namely Big Phil.
Luiz Felipe Scolari became the manager of Chelsea at the start of 2008-09 and began the campaign with a bang. The Blues were in hot form at the start of the season, with Anelka being the star of the show. But after a 2-1 home defeat to Arsenal, things went south.
Chelsea did not have a good December and January, as they dropped out of the title race. After a 2-0 defeat to Liverpool and a 0-0 draw at home to Hull City, Scolari was sacked and became the third Chelsea manager to leave in the past two seasons. Ray Wilkins was the interim manager for an FA Cup game before Guus Hiddink was appointed as caretaker boss until the end of the season.
He did a great job in stopping the downfall and helped to steady the Blue ship. He was the fourth Chelsea manager in two seasons, truly epitomizing how cut-throat the managerial job at Chelsea really is.