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Chelsea have managed to attract some of the biggest stars in world football to Stamford Bridge since Roman Abramovich rocked up in 2003, but they've also let a number of top talents slip through their fingers.
Abramovich's arrival in west London preceded 18 trophy-laden years for the Blues, who have won five Premier League titles, as many FA Cups, three League Cups and two Champions Leagues under his ownership.
The Russian has signed some iconic names over the years to make those triumphs happen, such as Didier Drogba, Eden Hazard, Diego Costa, N'Golo Kante and Ashley Cole.
However, Chelsea also have an unbelievable XI of players they perhaps let go a little too soon, which we've put together below…
The Belgian goalkeeper spent three years on loan at Atletico Madrid after first signing for Chelsea in 2011 and returned in 2014 with a La Liga winners' medal.
Courtois helped the Blues claim Premier League glory in two of his first three seasons at the Bridge, before leaving in 2018 to join Real Madrid – where he won another La Liga title in 2019/20.
A product of the club's academy, Ake only made 17 appearances in five professional years at Chelsea and spent the majority of his time out on loan.
The Dutchman departed in 2017 and signed for Bournemouth, where he impressed enough to earn a £41million switch to Manchester City last year.
While his time at City has so far been plagued by injuries, at 26 years of age he still has his best years ahead of him.
Who do you think is Chelsea's biggest transfer regret? Let us know in the comments section below.
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Tomori gained plenty of admirers when he burst onto the scene under Frank Lampard in the 2019/20 campaign, but for reasons which remain somewhat of a mystery he fell out of favour the following season.
The 23-year-old sealed a switch to AC Milan back in January and is already showcasing his quality at the San Siro, with England boss Gareth Southgate recalling him to his squad this month.
The France centre-back spent seven years at Chelsea after joining from Saint-Etienne in 2014, playing an important part in their 2014/15 Premier League title win.
After a series of loan moves he became a key member of Lampard's side from 2019 up until the start of this year, but he lost his place in the team when Thomas Tuchel arrived in January.
Zouma moved to West Ham this summer and, at 26, could go on to prove Tuchel and the Blues wrong for letting him go.
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A one-season wonder at Stamford Bridge, Luis completed a £16million transfer from Atletico Madrid in 2014 and helped Jose Mourinho's men win the Premier League title that season.
The Brazilian left-back returned to Atletico only a year into his Chelsea stint, reaching the Champions League final again in 2016 and capturing the Europa League in 2018.
Kevin De Bruyne
The masterful Belgian midfielder is without a doubt one of Chelsea's biggest transfer regrets, having been offloaded by Mourinho after just one season at the club in 2013/14.
He signed for Wolfsburg and showed enough potential for Manchester City to pay a club-record £55million fee for him in 2015, which raised eyebrows at the time.
But that fee has proved a bargain over the past six years, with De Bruyne developing into one of the best midfielders in world football under Pep Guardiola. A true disaster for the Blues.
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While they won't regret his departure as much as De Bruyne's, Chelsea may have benefitted from keeping Romeu around for longer than his two-year stint at the Bridge from 2011-13.
The Spanish midfielder performed so well in his debut campaign that ex-club Barcelona were tempted to activate their buy-back clause, but Mourinho deemed him surplus to requirements upon his return in 2013.
After loans at Valencia and Stuttgart, Romeu joined Southampton in 2015 and has been a consistent performer for the mid-table Premier League outfit.
Another major regret, Salah has made Blues chiefs look foolish for sanctioning his departure in 2016.
Following a decent campaign at Roma, Liverpool forked out £37million to bring him to Anfield, where he has etched his name into footballing folklore.
The Egyptian, who stokes a claim to being the best player in the world right now, has scored a frightening 134 goals in 212 games for the Reds, winning the Premier League and the Champions League. Another nightmare for Chelsea.
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The Spanish playmaker was voted Chelsea's Player of the Year in each of his first two seasons at Stamford Bridge and won the Champions League in 2012, but Mourinho's return a year later marked the beginning of the end for him in SW6.
Having struggled for game time under the Portuguese, Mata left to join Manchester United in 2014, where he remains today.
While his time at Old Trafford hasn't been majorly successful, there is still a feeling of what could have been for Mata at Chelsea.
Robben got his hands on two Premier League titles with Chelsea and was at the top of his game before injuries essentially ruined his third and final season at the club.
Mourinho therefore allowed the Dutchman to go to Real Madrid in 2007, but it was at next club Bayern Munich where he would enjoy his greatest success, winning eight Bundesliga titles and the Champions League while cementing his status one of the best attackers on the planet.
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It is certainly too early to say Chelsea regret selling the 24-year-old, however his early form at Roma suggests they very much could do later down the line.
Abraham netted 30 goals in 79 appearances for the Blues, only to fall dramatically out of favour under Tuchel earlier this year and subsequently be offloaded to Italy.
He has already recorded four goals and three assists for Roma, meaning he was recalled to the England squad by Southgate this month.
- Mohamed Salah
- Chelsea FC
- Manchester City FC
- AS Roma FC
- Liverpool FC
- Manchester United FC
- AC Milan FC
- West Ham FC
- Real Madrid FC
- Southampton FC
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