Ranking the 5 greatest Chelsea managers of the Roman Abramovich era

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

Chelsea Football Club was taken over by Russian billionaire Roman Abramovich in 2003. It's been 18 years since and the London club has seen a lot of success in the process.

Under the ownership of Roman Abramovich, Chelsea have had several managers. The Russian is known to have less tolerance for low rates of success, which is why plenty of managers have got the boot under his ownership.

Chelsea have appointed some world-class managers in the Roman Abramovich era

Some well-known managers like Rafael Benitez, Maurizio Sarri, Luiz Felipe Scolari and others have struggled at Chelsea in the past. They have failed to impress Roman and were inevitably sacked irrespective of that stature.

While that is true, it is also a fact that some managers have done amazingly well at Chelsea under Roman Abramovich's ownership. They have brought success and in a way given a new identity to the club. On that note, let's take a look at the five greatest Chelsea managers to have taken charge at the club in the Roman Abramovich era:


#5 Roberto Di Matteo

Roberto Di Matteo had a successful spell in his nine month as Chelsea's manager
Roberto Di Matteo had a successful spell in his nine month as Chelsea's manager

The former Chelsea midfielder divides opinion when it comes to his managerial career with the Blues. Roberto Di Matteo was assistant to then Chelsea manager Andre Vilas-Boas in 2011. As things did not go Vilas-Boas' way, he was sacked in March 2012, with Di Matteo becoming the interim manager.

The Italian had an amazing start to his Chelsea career as within almost two months he helped them win both the FA Cup and the UEFA Champions League. It was the first Champions League trophy in the history of the London club. It came as a surprise to many given Di Matteo's managerial experience but he made the impossible possible.

The following season, Di Matteo was made Chelsea's permanent manager. He started with losses in the FA Community Shield and UEFA Super Cup but had a good start to the Premier League. Over time, his team struggled in the UEFA Champions League and were eliminated in the group stages, which is when he was let go of his role. Many pundits claimed the move was uncalled for given his achievements in the previous season.

However, Chelsea have always been known for being result-oriented and the decision did not surprise many, even though it felt slightly harsh. Di Matteo was the mastermind behind arguably the greatest ever turnaround in the club's history when they won the Champions League in 2012.

Everything about the campaign was magical and it is highly unlikely that Chelsea would experience something that trumps it anytime soon. As such, the former Chelsea player and manager will certainly go down as one of the most affable gaffers at the club.


#4 Thomas Tuchel

Thomas Tuchel can achieve big things with Chelsea
Thomas Tuchel can achieve big things with Chelsea

The German manager has quite the experience under his belt. Thomas Tuchel has done considerably well with clubs like Borussia Dortmund and Paris Saint-Germain (PSG).

Following the sacking of Frank Lampard as Chelsea's manager in January 2021, Tuchel was signed to replace the club legend. He's the first German ever to manage the Blues. With his technical knowledge and impressive tactics, the former PSG manager was able to turnaround the London club's form in every competition. His strategy to use a three-man defense worked wonders.

Tuchel guided Chelsea to the FA Cup final after they defeated Manchester City 1-0 in the semifinals. They eventually lost to Leicester City in the final but it was an impressive run. The German manager's major success came in Europe as, against all odds, Chelsea defeated Manchester City to win their second Champions League trophy.

Chelsea also won the UEFA Super Cup at the start of the ongoing season and are looking very strong in the Premier League. Thomas Tuchel looks likely to lead Chelsea to further heights, but then again predicting the course of managers at this club would be naive, as history suggests.

#3 Antonio Conte

Chelsea v Sunderland - Premier League
Chelsea v Sunderland - Premier League

Chelsea signed Antonio Conte as their new manager for the 2016-17 season following the departure of Guus Hiddink. The Italian had good credibility in his managerial career having won Serie A thrice with Juventus.

Conte was one of the preachers of the three-man defense but at Chelsea he initially started with a back-four. It was after going 3-0 down at Arsenal that Conte famously tweaked the system to his infamous 3-4-3 and the rest is history.

The Blues endured a remarkable run of form on the pitch and, as a result, won the Premier League in Conte's first ever season in England. The following season, the Italian manager helped the London club win the FA Cup.

Unfortunately, Chelsea finished fifth at the end of the 2017-18 season which led to the sacking of Conte as the Blues missed out on a place in the Champions League. He was replaced by his fellow countryman Maurizio Sarri, who did not enjoy the best of spells at Stamford Bridge.


#2 Carlo Ancelotti

Chelsea v Newcastle United - Premier League
Chelsea v Newcastle United - Premier League

Chelsea have seen a good number of Italian managers at their helm and Carlo Ancelotti is arguably the finest of the lot. The former AC Milan manager has an immense amount of experience and is currently managing Real Madrid for the second time in his career.

Ancelotti signed for Chelsea in the summer of 2009. The following season, he led the team to the Premier League title with a margin of one point. That season was a memorable one for the Blues as they scored 103 goals in the league, the first team to achieve the feat in England's top-tier league. Chelsea also went on to win the FA Cup that season, completing the domestic double.

In the 2010-11 season, Chelsea finished second behind Manchester United in the Premier League. Despite that, Ancelotti was sacked by Roman Abramovich after which the Italian signed for Paris Saint-Germain. The Italian has now returned to former club Real Madrid for his second stint as manager.


#1 Jose Mourinho

Chelsea v Tottenham Hotspur - Capital One Cup Final
Chelsea v Tottenham Hotspur - Capital One Cup Final

Jose Mourinho kickstarted the revolution brought on at Chelsea under Roman Abramovich. He's easily the best manager in the club's history.

Following his heroics with Porto, the Portuguese manager joined Chelsea in 2004. His detailed understanding and analysis of the opponents made Jose Mourinho a very tactically sound manager. He was brought in by Roman to have an immediate impact and he did not disappoint. He won two Premier League titles, the FA Cup and two League Cups during his three seasons with the Blues.

Amidst rumors that Mourinho and Roman had a disagreement in 2007, the former left Chelsea to sign for Inter Milan, where he won a historic treble. After leaving his next job at Real Madrid, Mourinho eventually returned to Chelsea for a second spell in 2013.

Jose managed to win the Premier League once again with Chelsea in the 2014-15 season along with the League Cup. Much of what Chelsea are today has to do with how the Portuguese set the tone in the early days of Roman Abramovich's era.

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