Ranking every Chelsea manager of the Roman Abramovich era from worst to best 

Chelsea v Manchester City - Premier League
Chelsea v Manchester City - Premier League

With Maurizio Sarri leaving the club to join Juventus, the search is on for another person to take the reigns at Chelsea. The ever-revolving door has once again been pushed and ruthless Chelsea owner, Roman Abramovich is on the hunt for a new manager.

The Blues have become known for constantly changing managers, with a brief moment of failure being enough to see the club cut their ties with a coach. Despite the complaints from fans and the media, the policy has worked, with the club becoming one of the most successful teams in Europe.

Roman Abramovich has brought in a range of managers, from young upcoming talent to vastly experienced coaches, with varied success, but how do the Chelsea coaches rank?

With Chelsea legend, Frank Lampard the current bookies favourite, how will the next boss fare in comparison to the 11 men who have come before them?


Also see : EPL Transfer News, Copa America Standings, Womens World Cup Bracket


#11 Andre Villas-Boas (2011-12)

Tottenham Hotspur v Chelsea - Premier League
Tottenham Hotspur v Chelsea - Premier League

Everybody thought that Andre Villas-Boas was going to be the second coming of Jose Mourinho at Chelsea. Having worked with him previously and having plenty of buzz around him coming in, there was a lot of expectation for his arrival.

Sadly, things didn’t exactly go to plan for AVB at Stamford Bridge, struggling to make his mark in what would end up being a trophyless spell at the club as he was sacked within a year of being in charge.

Thankfully for the Blues, the season wasn’t a total bust as the club went on to win the double that season, including Chelsea’s famous Champions League victory.

But he wasn’t the man in charge to make it happen. Villas-Boas caused controversy by trying to push out some of the clubs old guard which the fans (and seemingly the squad itself) didn’t agree with, and that was his demise.

To this day Villas-Boas has the worst win percentage in the history of Roman Abramovich’s era, winning only 47.5% of his games as Chelsea manager.

#10 Felipe Scolari (2008-09)

Liverpool v Chelsea - Premier League
Liverpool v Chelsea - Premier League

Much like when Andre Villas-Boas joined the club, there was a lot of excitement surrounding Felipe Scolari when he was announced as the new manager, but that hope quickly faded away.

The former Brazil and Portugal boss had major success throughout his career and kick-started life at Chelsea with a positive start. Playing free-flowing attacking football and making impressive signings such as Deco, it seemed like Scolari was the right man for the job.

However, his stint at the club was very short-lived, although the club sat in the third place when he was fired. It seemed like the club was struggling to step up and challenge for the title which is never good enough for Chelsea.

With “communication issues” being stated as the reason for his departure, his tenure is not one that many fans remember fondly and is quite often forgotten about. Having won only 55.6% of the games he was in charge of, that isn't exactly a surprise.

#9 Claudio Ranieri (2000-04)

Tottenham Hotspur v Liverpool - UEFA Champions League Final
Tottenham Hotspur v Liverpool - UEFA Champions League Final

Claudio Ranieri was in-charge when Roman Abramovich bought the club, but only lasted one year and failed to win a single trophy during his four years as boss.

His greatest achievement as a manager is now seen as his incredible Premier League victory as Leicester City manager, but Ranieri also did a great job in building the platform that Chelsea sprung off in later seasons.

Ranieri had done well in the years leading to the club’s sale, overseeing the development of Chelsea legends John Terry and Frank Lampard.

Even though he won nothing, Ranieri took Chelsea to second place in the league, only falling short behind Arsenal’s impressive Invincibles, as well as guiding the club to the Champions League semi-finals, losing out to Monaco.

Had he been given a long spell in charge, then Ranieri would certainly have taken Chelsea to the next level, but unfortunately, his time was cut short. However, with a win percentage of just 53.8%, there is certainly a case that he wasn't quite ready to take Chelsea to the elite level.

#8 Avram Grant (2007-08)

The Championships - Wimbledon 2013: Day Six
The Championships - Wimbledon 2013: Day Six

Avram Grant’s appointment as Chelsea manager took a lot of people by surprise back in 2007, mainly because people didn’t really know who he was. The fact that he was the man to replace Jose Mourinho certainly added to the shock, with most thinking a major name would be brought in to help the club kick on.

The Israeli was a friend of Abramovich’s and had been the director of football at the club before taking the hot seat.

Despite the fact he wasn’t a big name, Grant actually did a very good job in charge and almost helped the club win three different titles. Although he ultimately won zero, which is why he found himself looking for a new club at the end of the season.

Grant’s side was defeated by arch-rivals Tottenham Hotspur in the League Cup final and managed to push Manchester United all the way until the final day of the season in the hunt for the Premier League title.

However, the biggest achievement and failure for Grant was in Europe. Having guided Chelsea to the Champions League final, he was on the cusp of making history with the Blues until John Terry’s slip as the Red Devils claimed Europe’s top prize.

Despite the fact he still remains the least known name on this list, Grant still claims the highest win percentage in the Abramovich era, with a very impressive 66.7%.

#7 Rafa Benitez (2012-13)

Fulham FC v Newcastle United - Premier League
Fulham FC v Newcastle United - Premier League

Rafa Benitez may very well have been the most unpopular manager in the Roman Abramovich era, mainly due to his previous spell in charge of Liverpool, but if you take away the Chelsea fans’ feelings, he did a great job as the boss.

He didn’t inherit the strongest squad in the clubs history, but Rafa did a superb job in steadying the ship, even though it was very clear that he wouldn’t be a long-term manager at the club.

However, having won 58.3% of his games in charge, a strict look at just the performances of his side provided a strong indication that he could have done a fine job as the manager for a longer period.

Despite serious hate from his own fans, he managed to stay level headed and got on with the task at hand, guiding the team to a Champions League position for the club to build on the following year.

Rafa also brought a trophy back to Stamford Bridge, winning the Europa League, which made them the only team to hold both European trophies simultaneously (until a few days later when a new Champions League holder was crowned).

#6 Guus Hiddink (2009, 2015-16)

Chelsea Press Conference
Chelsea Press Conference

Guus Hiddink was brought in twice by Roman Abramovich when the club was in desperate need for a manager, but only one of his reigns was a success.

His first spell in charge during 2009 saw the Dutchman lead Chelsea to FA Cup glory, losing only once in the 22 games he was in charge, finishing second place in the Premier League.

His impressive work as the interim manager led many Chelsea fans to want him in charge full-time, but Hiddink opted to continue his work as the Russian national team's head coach instead.

During his second season, Hiddink had a mountain to climb, taking over the club who were sat 16th in the league table. Hiddink managed to drag the team to a 10th place finish, but for Chelsea, that simply is not good enough.

Hiddink also saw his side fall out of the Champions League to PSG, as well as losing in an FA Cup quarter-final, which is why he wasn’t kept on long-term. His two reigns combined left Hiddink with a win percentage of just 53.1%, which is actually the second worse of the Abramovich era, a lot of which is down to his second spell.

#5 Maurizio Sarri (2018-19)

Chelsea v Arsenal - UEFA Europa League Final
Chelsea v Arsenal - UEFA Europa League Final

The latest victim of Roman Abramovich’s ruthless reign did a much better job than most Chelsea fans or members of the media were willing to give him, which is one of the main reasons he happily returned to Italy to manage Juventus.

The expectation had been high for Maurizio Sarri, as it is with every manager, in the hopes he could implement his infamous ‘Sarri Ball’ at the club. However, his refusal to play youth and his lack of an option B in terms of tactics quickly turned the fans against him.

But despite those issues, Sarri managed to have a successful first season in England, guiding Chelsea back to a Champions League position with a third-place finish and winning the Europa League in the same season.

Sarri also managed to take the club to a League Cup final, only to lose out on penalties to Manchester City. However, he wasn’t given a chance to develop and kick on, but his one season was an impressive one.

Winning over 61% of his games in charge, taking the club to two cup finals and earning a Champions League spot, it will always remain a big 'what if' in regards to how far Sarri could have taken the club.

#4 Roberto Di Matteo (2012)

Juventus v Chelsea FC - UEFA Champions League
Juventus v Chelsea FC - UEFA Champions League

The only manager to take Chelsea to the pinnacle of European football, Roberto Di Matteo enhanced his own Chelsea legend by winning the Champions League with the Blues against all odds.

Even though he had a real lack of experience when he took over, Di Matteo, who was working as Villas-Boas' assistant at the time, certainly left his mark on the club.

A two-goal comeback against Napoli, and victories over Benfica, Barcelona, and eventually Bayern Munich in the Allianz Arena saw one of the greatest Champions League victories in the history of the competition.

However, in the league, the Blues finished sixth and only qualified for the following season's Champions League by winning the competition. The following season saw a poor start to life as the manager for Di Matteo, being knocked out of the Champions League at the group stage, which brought his time in charge to an abrupt end.

The Chelsea legend managed a win percentage of 57.1%, which plants him in the middle of the Abramovich era. However, being the only man to bring in the Champions League adds a lot of weight to his claim at being the best boss under Abramovich.

#3 Antonio Conte (2016-18)

Chelsea v Manchester United - The Emirates FA Cup Final
Chelsea v Manchester United - The Emirates FA Cup Final

Antonio Conte arrived at Stamford Bridge having to fix a broken Chelsea FC, fresh off a 10th-place finish. Conte had the seemingly impossible job of transforming the side into a title contending team once again.

Despite a tough start to life at the Bridge, Conte did manage to turn things around with an incredible 13-match unbeaten streak that saw him guide the Blues back to the top of the mountain, winning the Premier League in his first season.

Conte set a Premier League record (which has since been broken by Manchester City), winning 30 games in one season and managed to reach the FA Cup final in both of the seasons he was in charge.

However, Roman Abramovich's impatience was clear, sacking Conte after his second season due to him failing to win a trophy. It was a baffling decision that many didn't agree with at the time due to how well he had done in charge of the Blues, but was a perfect example of why managers fail to stay long term at the club.

Only Avram Grant boasts a better win percentage than Conte, who won 65.1% of his games in charge. And when you consider how many more games he was the boss for, his stats really are very impressive.

#2 Carlo Ancelotti (2009-11)

Arsenal v S.S.C. Napoli - UEFA Europa League Quarter Final: First Leg
Arsenal v S.S.C. Napoli - UEFA Europa League Quarter Final: First Leg

The popular Italian was another victim of the second season syndrome at Chelsea FC, with Roman Abramovich refusing to show any patience with him after failing to pick up any trophies in his second season in charge of the club.

With a 61.5% win ratio, Carlo Ancelotti guided Chelsea to the double in his first season, winning the Premier League and the FA Cup for the first time ever in a fantastic campaign that saw the Blues play some of their best football.

Chelsea was free-flowing and attacking, scoring a record-breaking 103 goals in the league, which has only been recently topped by Manchester City. Chelsea scored more than seven goals in a game on four occasions, including an emphatic 8-0 win over Wigan Athletic.

Unfortunately, a poor second season that saw Chelsea gain just 71 points in the league brought an end to his time in charge, a lot earlier than many fans would have liked.

#1 Jose Mourinho (2004-07, 2013-15)

Chelsea FC v Manchester United - Premier League
Chelsea FC v Manchester United - Premier League

Even though both of his reigns as Chelsea boss ended in fallouts, Jose Mourinho remains not just the greatest manager of Roman Abramovich’s era, but in the club’s history altogether.

The Special One is still beloved by most fans at Stamford Bridge and with a brilliant 63.6% win percentage over two spells that saw him win three Premier League’s, three League Cups and an FA Cup it is hard to argue against it.

Mourinho is the manager who helped put Chelsea on the map, taking the club to new heights as the Blues dominated English football and quickly became a force to be reckoned with across Europe as well.

Mourinho had bags of charisma and created some iconic moments from shushing the Liverpool fans to his witty one-liners to the press. All of this helped him win over the fans.

Of course, there were plenty of dark times during his tenure as well, with both of his runs ending in major fallouts and poor runs of form, but overall his time in charge was a big success.

Whether he was the Special One or the Happy One, ultimately, he was the successful one and in this game, you are judged on exactly that.

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