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#3 Luiz Felipe Scolari
Scolari signed for the Blues in 2008. The former World Cup winning manager endured a disastrous spell in 2008-09 where he did not last through the season.
After just seven months in charge, Scolari was ousted despite going the first twelve games undefeated. He also reached the final stages of the Champions League and FA cup, before enduring a painful run of just three wins in nine Premier League games
"Big Phil" Scolari joined Chelsea in a summer which saw the likes of Deco and Ricardo Quaresma come in
He had publicized fallouts with Michael Ballack, Nicholas Anelka and Didier Drogba. He also famously had to use a translator to convey tactical and management advice. Due to these reasons, Scolari was on the chopping block as Abramovich demanded success.
In came Guus Hiddink, who lost just one game in 20 to lead Chelsea to the 2009 FA Cup. He was narrowly pipped by Barcelona and Manchester United in the Champions League and Premier League respectively.
#2 Andrea Villas-Boas
Young Andre Villas-Boas was brought in as a "chosen one," in 2011, having had a Chelsea connection since he was part of Jose Mourinho's backroom staff.
He went on to replicate Mourinho's success at Porto by winning the Europa League the previous season. This led to his appointment in 2011, despite being younger than some of his players.
Carlo Ancelotti was almost cruelly sacked after a disappointing second place finish and Champions League knockout against Manchester United. In came Villas-Boas with the hope of delivering the holy grail Champions League trophy.
Few would have predicted that Chelsea would deliver on that promise in his very first season. Though it was without him as manager as he was sacked halfway between the campaign.
When he arrived he shook things up at the club. He made personnel and tactical changes such as playing a very high defensive line and leaving club captain John Terry on the bench.
Roman Abramovich yearned for attacking football. However 10 lossess and 11 draws in his 40 games led to disarray at the club. Famous 5-3 losses to Arsenal, 3-1 to Napoli and 1-0 at home to West Brom turned out to be the final straw for the young Portuguese manager.
#1 Roberto Di Matteo
It is hard not to grant credit to Roberto Di Matteo's legacy of being the first ever Chelsea manager to win the Champions League.
He was signed in March 2011 after the sacking of Andre Villas-Boas.
He had the miraculous achievement of leading Chelsea through its greatest moment. Despite that, he is often considered the worst manager Roman Abramovich has taken on at the club based on his inexperience.
Di Matteo won just 24 games out of his 42 in charge, scoring a mere 43 goals, and looked considerably out of depth in a tame Chelsea set-up. He had Fernando Torres and Daniel Sturridge as the only two recognized strikers in the squad.
The disastrous 3-0 defeat against Juventus was where he publicly dropped Fernando Torres at centre-forward. He went with Eden Hazard as a false nine. The defeat signaled the end of the line for the still fondly loved and respected Italian.
