All 13 of Roman Abramovich’s Chelsea Managers Ranked From Best to Worst

Chelsea owner Roman Abramovich showed time after time that he can be ruthless, as evidenced by the range of managers that he employed at the West-London club after completing his takeover of the club in 2003.

While some managers were a resounding successes, others struggled immensely. Some of the most famous names in football have managed Chelsea, with Abramovich’s era witnessing five league titles.

But winning league titles, and even the Champions League, has not afforded some managers time. It is open for debate as to whether or not Abramovich’s trigger-happy ways were positive for the club or not.

In this article, we count down each of the Chelsea managers that passed through the club during Abramovich’s era, starting with the worst, and finishing with the best.

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13. Andre Villas-Boas

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Andre Villas-Boas arrived at Chelsea in the summer of 2011 amidst significant fanfare. At the time, Villas-Boas had just become the youngest manager to have won a European title – which he achieved with Porto in his native Portugal.

Villas-Boas had been previously employed by Chelsea as an assistant coach to compatriot Jose Mourinho (more on him later). Chelsea paid a world-record £13.3million compensation fee to Porto for Villas-Boas.

Chelsea made an average start to the season, before defeats to Manchester United, Arsenal, QPR and Liverpool left Villas-Boas under pressure.

Villas-Boas appeared to fall out with some of Chelsea’s “old guard”, such as Frank Lampard, Ashley Cole and Michael Essien. Chelsea fell out of the top 4 in February 2012, and a defeat to West Brom in March 2012 resulted in Villas-Boas being relieved from his duties.

Villas-Boas came so highly-rated, but was unable to live up to the hype. One thing that should be mentioned is that Chelsea did go on to win the Champions League that season, with Villas-Boas contributing to this.

12. Luiz Felipe Scolari

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Seeking an elusive Champions League title, Roman Abramovich appointed highly-rated, World Cup-winning coach Luiz Felipe Scolari. It seemed that a man of his pedigree would be what was needed to take Chelsea to the next step.

On paper, it was a match made in heaven. But what actually happened was a total disaster. Eyebrows were raised from the outset after Scolari admitted that part of the appeal of Chelsea was financial, with Scolari handed a high wage.

Chelsea started the season strongly, and sat top of the table for the first few months of the season. Their incredible run of avoiding defeat in 86 home games was ended against Liverpool, with Chelsea also knocked out of the League Cup by the then-Championship side Burnley.

A run of draws and sporadic defeats put Scolari on the brink. A heavy 3-0 defeat to title rivals Manchester United, and another defeat to Liverpool left Chelsea in 4th place. A goalless draw with Hull City eventually spelled the end of Scolari’s ill-fated reign in February 2009.

11. Frank Lampard

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As a legend of the club, Frank Lampard was a popular appointment to the managerial role in the 2019-20 season. Lampard had impressed while managing Derby. But owing to transfer activity, Chelsea were banned from signing any players, which made life difficult for Lampard.

Chelsea also lost influential playmaker Eden Hazard, and started the Premier League season with a poor 4-0 defeat to Manchester United. But results soon picked up, and Chelsea were consistently in the top 4 as the months went by.

A poor run of form over the festive season threatened to derail their season, but they eventually qualified for the Champions League, placing 4th. Lampard was praised for promoting youth talent, placing highly despite the transfer ban, and his attacking football.

But there was to be further FA Cup disappointment for Chelsea, who once again lost to Arsenal in the final, while they were knocked out of the League Cup by Manchester United. Chelsea lost 7-1 on aggregate in the Round of 16 to Bayern Munich, and lost in the Super Cup to Liverpool.

Despite those setbacks, the first season was seen as a success, and Lampard was heavily backed in the transfer window for the 2020/21 season. Hakim Ziyech, Ben Chilwell, Thiago Silva, Timo Werner, Kai Havertz and Edouard Mendy were all among the high-profile acquisitions.

Chelsea made a stable start to the season, with too many draws seeing them struggle to keep pace with the league leaders. Defeat to Tottenham Hotspur in the League Cup was disappointing, though Lampard did guide Chelsea to the knockout phase of the Champions League.

But a poor run of form over the winter months ultimately ended Lampard’s Chelsea reign. Lampard departed Chelsea with them in a mid-table position. He did go out with a victory though, with Chelsea beating Luton 3-1 in the FA Cup.

Lampard ultimately paid the price for Chelsea’s inability to form a title challenge, and was replaced by Thomas Tuchel. Lampard’s true legacy might not be realised for some time, with the youngsters he blooded likely to make an impact for Chelsea for many years to come.

Lampard departed as a Chelsea legend, and as mentioned, his true impact on the club might not be truly appreciated until several years time.

10. Avram Grant

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A manager that perhaps deserved more credit was Avram Grant, who had the thankless task of taking over from Jose Mourinho during the 2007-08 season.

He entered the club as a virtual unknown to the majority of people outside of his native Israel – where he had to his credit enjoyed success.

He inherited a high-quality, but underperforming squad. But he quickly arrested the club’s poor form, and eventually led Chelsea to a title-charge. The blues gradually reeled in leaders Arsenal and Manchester United.

But Manchester United would prove to be the scourge of Grant. Firstly, Chelsea missed out on the Premier League 2007-08 title, with Chelsea finishing second to United. They then lost in the Champions League final to United.

Grant was a John Terry slip away from winning the Champions League, but cruelly missed out. This would prove to be Grant’s final game with Chelsea, as he made way for the ill-fated reign of Scolari.

But Grant deserves credit for his 2007-08 performance, and actually remains the manager with the highest points per match rate with the club – though there was no silverware, which ultimately proved to be his downfall at Chelsea.

9. Maurizio Sarri

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Maurizio Sarri is a polarising figure among Chelsea fans. The Italian spent just one year at the club from 2018-19, having taken over from compatriot Antonio Conte. His famed “Sarri-ball” at Napoli had won him many admirers.

Chelsea made a very strong start to the season, winning eight of their first twelve games. But following a defeat to Tottenham Hotspur, Chelsea’s form became somewhat erratic, and they struggled to maintain a title challenge. They were beaten 6-0 by eventual champions Manchester City in what was the low point of the season.

Despite inconsistent form, Sarri guided Chelsea to a respectable 3rd place finish, and helped the club qualify for the 2019-20 Champions League. While his playing style didn’t win him too many fans, Chelsea had impressed under his stewardship.

Chelsea were knocked out of the FA Cup by Manchester United, and lost in the final of the League Cup to Manchester City on penalties. The latter is infamously remembered for Chelsea goalkeeper Kepa Arrizabalaga disobeying Sarri’s substitution, in what amounted to an embarrassing situation for the club.

But the high point of the Sarri reign was certainly the Europa League, which Chelsea won. While they had a somewhat simple route to the final, they played superbly in the final itself, beating rivals Arsenal 4-1.

Sarri left Chelsea at the end of the season to take charge of Italian giants Juventus. It will never be known just how far Sarri would’ve taken Chelsea, but he departed the club leaving them in good shape.

8. Claudio Ranieri

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Claudio Ranieri was the first manager of the Abramovich era, with the Russian oligarch taking over the club in the summer of 2003. Ranieri had been the manager of Chelsea for a few seasons, and so it made sense for Abramovich to stay with Ranieri as he acclimatised to English football.

Abramovich stepped his mark on the club by bankrolling a spending spree of £110million, with players such as Geremi, Damien Duff, Joe Cole, Juan Sebastian Veron and Adrian Mutu all being recruited. The two marquee signings were Claude Makelele from Real Madrid and Hernan Crespo from Inter Milan.

Chelsea started the season in style, winning six matches from their first seven, including an opening-day victory over Liverpool at Anfield. A first defeat of the Abramovich era away at Arsenal didn’t dampen Chelsea’s spirits, as they bounced back with five straight victories.

But Chelsea were unable to maintain a title challenge, and their season unravelled with a run of just three wins in eight matches, including defeats to Bolton and Charlton. A home defeat to Arsenal curtailed any chance of a title push, with Arsenal going on to win the title with an unbeaten record.

Chelsea eventually finished runner-up’s in the league, representing their best finish for decades. They also cruised through to the knockout stages of the Champions League, where they made it to the semi-final stage. But Chelsea suffered a disappointing aggregate defeat to AS Monaco, ending their hopes of Champions League glory.

Chelsea were knocked out of both the FA Cup and the League Cup in the formative rounds. Despite Ranieri achieving Chelsea’s best league finish, and a run to the last four of the Champions League, he was sacked at the end of the season. Ranieri went on to win the Premier League with Leicester City in the 2014-15 season.

7. Rafael Benitez

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Rafael Benitez was appointed as Chelsea manager in November 2012, after replacing Roberto Di Matteo mid-season. Benitez was a very unpopular choice among Chelsea fans, with many booing Benitez upon his arrival. Benitez was unpopular owing to the fact that he had made disparaging remarks about Chelsea while Liverpool manager, and the fact that he replaced club legend Di Matteo.

Chelsea made a rather low-key start to the Benitez era, with three successive draws leaving them seven points behind leaders Manchester United. Chelsea were knocked-out of the Champions League in the group stage, lost in the FIFA Club World Cup final, and were embarrassingly beaten by rivals QPR at home.

But their form did pick up during 2013. They excelled in the Europa League knockout stage, and a run of eight games without defeat to finish the Premier League season allowed them to finish in 3rd place. This represented a strong turnaround for Chelsea, and Benitez received credit.

Chelsea made it to the Semi-Final of the FA Cup, but fell to Manchester City, while they fell at the same stage to Swansea in the League Cup. But Chelsea did succeed in the Europa League, going all the way to the final, where they beat Benfica to clinch Europa League glory.

Benitez was far from popular during his Chelsea reign, and he himself criticised the Chelsea board for labelling him as the “interim” manager. But he impressed during his stint, having helped Chelsea finish in the top 4, and securing another European trophy.

6. Guus Hiddink

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Experienced Dutchman Guus Hiddink has had two spells as Chelsea manager – once in 2009 after taking over from Luiz Felipe Scolari, and again in 2015 after he took over from Jose Mourinho. On both occasions Hiddink was the caretaker manager, and acted as a calming presence, with the task of steadying the ship.

Hiddink had a remarkably impact in his first spell. After taking over in February, Hiddink oversaw a run of four consecutive victories in the league. Chelsea were unable to mount a title challenge, with Manchester United and Liverpool duelling it out – with United once again coming out on top.

Hiddink won 11 of his 13 Premier League games, helping Chelsea secure Champions League football. He had further success in cup competitions too. He guided Chelsea to FA Cup glory, with the Blues defeating Everton 2-1 in the final.

Chelsea also advanced to the semi-finals of the Champions League, having seen off Juventus and Liverpool under Hiddink. They played Barcelona in the semi-final stage, and had it not been for a last-minute Andres Iniesta goal for Barcelona, Hiddink would also have guided Chelsea to the Champions League final for a second consecutive year.

The semi-final against Barcelona is infamously remembered for witnessing one of the most diabolical refereeing performances of all time, with Chelsea having numerous penalty appeals turned down. Hiddink departed at the end of the season, amidst heavy praise.

Six years later, in the 2015-16 season, Hiddink would return to Chelsea once more. After Jose Mourinho’s second reign ended in chaotic circumstances, Chelsea turned to Hiddink in late December, perhaps seeking a soothing, calming presence after the heavy-metal reign of Mourinho.

Hiddink was unable to replicate the success of his first reign, but once again impressed, and helped Chelsea from 16th when he took over, up to 10th. Hiddink’s Chelsea lost to Everton in the FA Cup, and were knocked out by PSG in the Champions League.

While Hiddink’s second reign with Chelsea was rather underwhelming, he is fondly remembered by Chelsea fans.

5. Antonio Conte

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Italian livewire Antonio Conte managed Chelsea from 2016-2018. After joining from Italy, Conte’s men made a strong start to the Premier League, with three wins in their first three games.

But a poor run in September followed, culminating in a heavy 3-0 defeat to Arsenal. But this was the catalyst for a formation change that would transform Chelsea’s season. Conte switched to a back three, and the transformation was remarkable.

An incredible run of 13 straight Premier League victories followed, including wins over Manchester United, Tottenham Hotspur and Manchester City, before they were beaten 2-0 by Tottenham. Their form picked up once again though, and only two other defeats followed.

Chelsea eventually cruised to a third Premier League title, with Conte’s men finishing 7 points clear on an excellent 93 points. They were simply fantastic, and Conte was widely praised for his tactics and ability to get strong performances from players.

Chelsea also went all the way to the FA Cup final in 2017, but were beaten by Arsenal, and they were knocked out of the League Cup by West Ham. With no European football played for Chelsea owing to their poor 2015-16 season, they were able to focus exclusively on domestic competitions.

Chelsea were unable to maintain their high level of performance in the 2017-18 season. After spending almost £200million on a host of players, they were unable to make a strong title challenge. They lost in the Community Shield to Arsenal, and followed it up with a home defeat to Burnley on the opening day of the season.

Despite then going five games unbeaten, defeats to Manchester City and Crystal Palace threatened to derail a budding title challenge. Manchester City became the runaway leaders, and Chelsea were unable to keep with them, eventually falling into a battle for the top four.

A run of five defeats in seven games pushed Chelsea out of the top 4 places, and despite a late rally, Chelsea ultimately finished 5th, meaning they failed to qualify for the Champions League. Chelsea did however win the FA Cup, defeating Manchester United in the Final.

Chelsea bowed out of the League Cup at the Semi-Final stage, and were eliminated in the Round of 16 by Barcelona in the Champions League. Despite two trophies in two years, Conte was sacked by Chelsea at the end of the season in a decision that many criticised.

4. Roberto Di Matteo

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Roberto Di Matteo was originally first-team coach under Andre Villas-Boas, but after Villas-Boas was dismissed, Di Matteo stepped into the manager’s hot-seat. Di Matteo had played for Chelsea in his playing career, so was well-used to Chelsea.

Di Matteo took over in March, so he didn’t have long to make an impact. But he made a remarkable impact – while their league form was patchy to say the least, Di Matteo’s side thrived in cup competitions.

Di Matteo guided Chelsea all the way to FA Cup glory, defeating Liverpool in the final. But this paled in comparison to Chelsea’s biggest achievement, with Di Matteo’s side winning the Champions League.

Chelsea saw off Napoli, Benfica and then vanquished the hoodoo of Barcelona to reach the final. The final was against Bayern Munich, and took place at Bayern’s Allianz Arena. Chelsea fell behind, but Didier Drogba equalised with minutes remaining. Chelsea went on to claim victory on penalties.

Di Matteo finally delivered what Roman Abramovich had been dreaming of – the elusive Champions League title. He became permanent manager in the summer, but couldn’t replicate his success in the 2012/13 season.

Defeat in the Community Shield to Manchester City was a disappointment, but Chelsea started the campaign strongly, winning 7 of their first 8 games before being beaten by Manchester United.

That defeat was the start of a four game run in the league without victory, while they also lost heavily to a Radamel Falcao-inspired Atletico Madrid in the European Super Cup. They were beaten 3-0 by Juventus in the Champions League, leaving Chelsea at risk of dropping out of the Champions League at the group stage.

Despite only winning the Champions League six months earlier, Di Matteo was sacked after Abramovich once again wielded the axe. Fans were outraged by Di Matteo’s sacking, and continue to remember him for his success. He will always be remembered for leading Chelsea to the Champions League.

3. Carlo Ancelotti

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Carlo Ancelotti came to Chelsea as a multiple-time Champions League winning manager, and with an incredibly CV. Ancelotti proved to be an excellent Chelsea manager, and his sacking was roundly condemned.

Ancelotti left AC Milan to join Chelsea in the close season of 2009. Despite a low profile transfer window, Chelsea impressed in the early months of the year. Ancelotti won the Community Shield in 2009, having seen off old rivals Manchester United in a penalty shootout.

Chelsea won their first match of the Premier League season courtesy of a last-minute Didier Drogba goal against Hull. Chelsea won their first six games of the season, before a surprise defeat to Wigan. Crucial wins over Manchester United and Arsenal left Chelsea five points clear at the top.

A shaky festive season saw Chelsea’s lead evaporate, though strong subsequent performances kept them top of the league. Chelsea eventually led the league going into the final matchday, with key wins over Manchester United and Liverpool helping them.

Chelsea emphatically sealed the league title with an 8-0 drubbing of Wigan, with Ancelotti winning the title in his first season. Ancelotti also excelled in the FA Cup, with Chelsea clinching the Cup after beating Portsmouth in the final. They lost to the Jose Mourinho-managed Inter Milan in the Second Round of the Champions League.

Following Chelsea’s most successful season in history, Ancelotti led Chelsea in the 2010-11 season, though they failed to hit the same heights. Another low-key summer transfer window took place, while Chelsea lost in the Community Shield to Manchester United.

Chelsea stormed to an early lead in the league, after winning their first five games. though Chelsea did lead the Premier League for much of the first half of the season. An erratic run of form took place over December, with a run of six consecutive games without a win, also featuring just 2 wins in 11 Premier League matches.

The addition of Fernando Torres for £50million proved to be ill-fated, though Chelsea did hit form. A run of 11 wins in 14 games left Chelsea just behind Manchester United heading into a crucial game at Old Trafford. Manchester United won the match 2-1, and went on to win the league.

Ancelotti’s side finished as runner-ups, and were also knocked out of the Champions League by Manchester United. They were also unable to retain the FA Cup, nor win the League Cup.

Following a trophyless campaign, Ancelotti was sacked as Chelsea manager. His sacking shocked many, with Chelsea fans left disappointed with the classy Italian’s departure. Ancelotti left as a highly-successful manager, and remains a firm favourite of Chelsea fans.

2. Thomas Tuchel

Thomas Tuchel ended up as the final appointment of the Abramovich era, which turned out to be a highly successful partnership. Tuchel was hired in 2021 to replace Frank Lampard. Tuchel had a mid-season start, but was able to quickly implement his methods.

Tuchel had a rather slow start to life in England, but the German soon presided over an upturn in fortune. Chelsea were unbeaten in their first 14 games under Tuchel, and also progressed to the final of the FA Cup, albeit in a losing effort to Leicester.

But the best moment for Tuchel was leading Chelsea to their second Champions League title in the 2021-22 season. Tuchel was widely praised for this – having only been managing the club for a few months. They knocked out Atletico Madrid, FC Porto and Real Madrid en route to the final.

In the final, Chelsea beat Man City 1-0 courtesy of a Kai Havertz goal. Tuchel was given a contract extension following the match, and went into the 2022-23 season targeting Premier League glory.

The 2022-23 season wasn’t as successful for Tuchel and Chelsea. They had entered the season aiming to challenge for the Premier League, but after a promising start, they were unable to keep pace with Man City and Liverpool. Chelsea did finish 3rd, meaning they secured Champions League qualification.

Tuchel did add to his trophy haul however by winning the UEFA Super Cup and FIFA Club World Cup. Chelsea unfortunately lost both domestic cup finals on penalties to Liverpool, in a cruel stroke of misfortune. The blues were knocked out of the Champions League by Real Madrid.

The Abramovich era ended at the end of the 2021-22 season, with a Todd Boehly led consortium taking over the club. Abramovich walked away, with Tuchel being his final coach.

1. Jose Mourinho

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Who else but the enigmatic Jose Mourinho can top this list? Mourinho has simply been a legendary manager for Chelsea, ushering in an era of dominance after his 2004 arrival, and later returning to the club to help secure further glory. While these days he doesn’t have huge amounts of Chelsea fans being in favour of him, when the dust settles, he will be remembered fondly.

Mourinho arrived at Chelsea in the summer of 2004 as the first appointment of Roman Abramovich. Mourinho had just guided FC Porto to an unexpected Champions League title. His first press conference proved memorable, with Mourinho announcing himself as “the special one”.

He lived up to the billing in his first season, as Mourinho’s Chelsea crushed the competition. Mourinho was heavily backed in the transfer window. Paulo Ferreira and Ricardo Carvalho followed Mourinho from Porto, while Petr Cech, Arjen Robben and Didier Drogba were other high profile arrivals. Mourinho also had a clear-out of sorts, selling the likes of Juan Sebastian Veron, Jimmy Floyd Hasselbaink, Jesper Gronkjaer and Hernan Crespo.

The Mourinho era started in style, with Chelsea beating Manchester United 1-0 on the opening day of the season. Five wins from the next seven would follow, before Mourinho’s first defeat as manager happened against Manchester City. Chelsea were remarkably defensively, keeping nine clean sheets in their first 12 games.

The defeat to Manchester City was the only defeat in the Premier League season. Chelsea ground out several wins over the Christmas period, and stretched away from Arsenal as the weeks went by. On Matchday 35 a 2-0 win away at Bolton assured Chelsea of the title, with Mourinho winning the league in his first season.

They ended the season with an incredible 95 points, finishing 12 points clear of Arsenal and 18 clear of Manchester United. Chelsea set many records – including the fewest goals conceded in a Premier League season (just 15), the most clean sheets (25), a then-highest points total in history, and numerous other records.

There was further Champions League heartbreak though for Chelsea, after they were knocked out by eventual winners Liverpool at the semi-final stage in acrimonious circumstances, with Liverpool’s “goal” not crossing the line.

Chelsea did however win the League Cup, beating Liverpool 3-2. They were knocked out of the FA Cup by Newcastle – but a league and Cup double represented a mightily successful campaign.

Chelsea continued to back Mourinho in the transfer market, albeit at lower levels than 2004. Shaun Wright-Phillips joined from Manchester City, while the arrival of Michael Essien from Lyon for £24million was a strong addition. Chelsea beat Arsenal in the Community Shield to gain another piece of silverware.

Chelsea made an incredible start to the 2005/06 season, winning their first nine matches of the season. They were beaten 1-0 by Manchester United on matchday 12, but bounced back in style by winning ten consecutive matches. A 2-0 victory over Liverpool at the start of February saw Chelsea move a whopping 15 points clear.

Defeats to Middlesborough and Fulham threatened to open up the title race, but a comprehensive 3-0 victory over nearest challengers Manchester United summed up their superiority. Two defeats in their final matches didn’t matter, as they still won by a margin of 8 points.

Chelsea weren’t able to secure anymore silverware in the 2005/06 season, with Barcelona knocking them out of the Champions League, London rivals Charlton besting them in the League Cup, and a defeat to eventual winners Liverpool in the FA Cup semi-final.

Despite this, two successive league titles had Mourinho’s stock at an all-time high. The 2006/07 season wasn’t as successful however. Andriy Shevchenko represented the club’s biggest investment at £30million, while Salomon Kalou, Ashley Cole and Michael Ballack were among others to join.

Chelsea lost in the Community Shield to old rivals Liverpool, but made a strong start to the Premier League season, winning 10 of their first 13 matches. But Chelsea did lose to Middlesborough and rivals Tottenham Hotspur. Chelsea were unable to pull clear of the chasing pack like they had in previous years.

Rivals Manchester United were rejuvenated, and despite nine straight victories for Chelsea between gameweek 25 and 33, Chelsea fell short of Manchester United. A 2-2 home draw with Bolton, coupled with a 4-2 come-behind victory from Manchester United against Everton, left Chelsea with little chance of winning the league.

Chelsea’s defence ultimately came up short after a 1-1 draw against Arsenal. Manchester United ultimately finished six points clear, with Chelsea unable to keep pace with them. Chelsea did get some revenge over Manchester United however in the FA Cup final, as the blues claimed the Cup with a narrow 1-0 victory. Chelsea also won the League Cup, beating Arsenal in the final.

Chesea had entered the 2006/07 season aiming for Champions League glory. For the third time in four years, Chelsea made it into the Semi Final stage, though rivals Liverpool got the better of them on penalties. It was a crushing blow once again for Chelsea.

Mourinho started the 2007/08 season hoping to regain the title. Chelsea only spent £20million in the summer, and lost in the Community Shield to Manchester United on penalties.

Over the first few weeks, Chelsea made a solid start, winning three of their first four matches. A 2-0 defeat to Aston Villa, followed by goalless draws with Blackburn Rovers and Rosenborg in the Champions League led to Jose Mourinho and Chelsea parting ways by mutual consent, ending an incredible marriage.

Chelsea fans voiced their disappointment with Mourinho’s departure. But six years later, the special one returned to the club after successful stints with Inter Milan and Real Madrid. Mourinho was given a hero’s welcome, and sought to repeat his previous success with the club.

Much of the spine of Mourinho’s original team remained, and Mourinho proclaimed himself to be “the happy one” in his first spell. Chelsea spent rather conservatively in the transfer market, with Willian at £30million their most expensive acquisition, though Samuel Eto’o was an exciting signing.

Chelsea made a solid start to Mourinho’s second reign of the club, and won six of their first nine fixtures. Defeat in the European Super Cup and early exits in the FA Cup and League Cup proved disappointing.

But Chelsea maintained a title challenge for much of the season, despite Mourinho referring to his side as a “little horse” that were not yet ready for a title battle. Damaging defeats to Crystal Palace and Sunderland put Chelsea all but out of contention.

With Mourinho’s Chelsea making it through to the Semi-Final of the Champions League, courtesy of victories over Galatasary and PSG, the Blues started to prioritise the Champions League.

Despite this, in what was hailed a “Mourinho masterclass”, a heavily understrength Chelsea side won 2-0 at Anfield against Liverpool, remembered for Steven Gerrard’s slip, and a remarkable rear-guard performance by Chelsea.

This did put Chelsea back in with a chance of title glory, but they ultimately placed 3rd, with Manchester City winning the league. Chelsea lost at the Semi-Final stage of the Champions League to Atletico Madrid, meaning Mourinho finished the season trophyless.

The 2014-15 season would prove much more memorable for Chelsea. Chelsea spent big in the summer transfer window, with Cesc Fabregas, Diego Costa and Filipe Luis among the arrivals, while Didier Drogba returned to Chelsea to much excitement.

Chelsea made a blistering start to the season, winning 11 of their first 14 matches, including victories over Arsenal and Liverpool. Chelsea lost just three times over the season, and a stable run throughout the later months of the season helped Mourinho clinch a third Premier League title with Chelsea.

Mourinho was hailed for the league success, with Chelsea spending most of the season at the top of the league. Chelsea won the title by eight points over nearest challengers Manchester City. Mourinho swept the managerial awards too.

Chelsea had mixed fortunes in the Cup competitions, an embarrassing exit to Bradford City in the FA Cup contrasted to yet another League Cup success for Mourinho, with Chelsea beating Tottenham in the Final. But Chelsea did fall to PSG in the Round of 16 of the Champions League.

The 2015-16 season ultimately spelled the end of Mourinho’s time at the club. It was a rather quiet window for Chelsea, with the £21.4million signing of Pedro from Barcelona the only noticeable signing. Radamel Falcao signed for what would turn out to be an ill-fated loan spell.

Mourinho signed a new 4-year contract at the start of the season. Chelsea started the season in disappointing fashion, having lost the Community Shield to Arsenal, which represented Mourinho’s first defeat to Arsene Wenger.

The first league game of the season turned out to be an infamous one. Chelsea drew 2-2 with Swansea in a match where Chelsea’s team doctor Eva Carneiro was heavily, and publicly criticised by Mourinho for running onto the pitch to treat Eden Hazard in the dying embers of the game.

This set the tone for Chelsea’s season. Mourinho’s men lost three times in the opening five games, and seemed to struggle badly for form. Despite the customary home win over Arenal, Chelsea finished October in poor form, and down in 15th.

Chelsea were doing strongly in the Champions League, but their league form continued to be poor, and they dropped to 16th in the league by the end of November. Further defeats to Bournemouth and Leicester City eventually led to Mourinho being sacked in mid-December.

The Chelsea fans furiously protested against Mourinho’s sacking. He left the club as a legendary figure, having clinched three titles with Chelsea and numerous other honours.

Mourinho’s popularity with Chelsea fans has somewhat dipped in recent years after he managed Manchester United and Tottenham Hotspur. But ultimately, Mourinho deserves credit for all he achieved at Chelsea, and remain their most successful manager – and certainly the best manager under Roman Abramovich.

Summary

During Roman Abramovich’s reign at Chelsea, some of the finest managers in the world led the club. His era was undoubtedly successful, and ended up with multiple trophies. Chelsea fans have showed significant support to Abramovich.

In May 2022, Abramovich’s time at the club came to an end, as he sold the club for £4.25billion. Going forward, it will be interesting to see how the new Chelsea regime do with the club – they will hope to usher in a new era of success.