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Five of Chelsea’s most bizarre managerial reigns

Oh Chelsea Football Club, you crazy, crazy b*stards! Let’s be honest when it comes to managerial mayhem, no other Premier League club can hold a torch to the Stamford Bridge outfit.

While many scoffed at the Blues making Frank Lampard the 14th manager of the Roman Abramovich era after Maurizio Sarri departed the club to take over as Juventus boss, nobody can laugh too much really, because if anything, all the last 16 years has proved is that the long-held belief that you need stability at a Football Club to be successful is complete and utter pony.


During the Russian Oligarchs reign as owner Chelsea have continued to pick up trophies – 16 in 16 years – by the bucketload, no matter how quickly they seem to go through coaches.

With that in mind, we’ve decided to take a look at five of the most bizarre Chelsea managerial reigns of the Abramovich era, although it was pretty tough picking five as they’ve all been a bit mental in their own way…

Avram Grant

Sept 2007 – May 2008

Israeli Grant was appointed as Chelsea’s Director of Football in the summer of 2007, mostly because of his close friendship with Blues owner Abramovich. Despite not even holding any relevant qualifications as a coach he was then thrust into the role of manager in the September of 2007, replacing Jose Mourinho.

Mourinho’s sacking did not go down well with the Stamford Bridge faithful and combined with Grant’s dour personality and glaring lack of experience he immediately became a hugely unpopular figure with the clubs fanbase.

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Even though Chelsea only narrowly lost out on the Premier League title, and finished runners up to Spurs in the League Cup, the general feeling was that the leadership group of John Terry, Petr Cech, Frank Lampard, and Didier Drogba had managed to maintain the clubs standards on the pitch, in spite of Grant.

It must be noted though that had it not been for Terry’s infamous slip against Manchester United in the Champions League final in Moscow, Grant would have gone down as the first Chelsea manager to deliver the Champions League. Grant’s tenure as Blues boss though is most commonly used to prove the old adage that ‘it’s not what you know, it’s who you know.’


Luiz Felipe Scolari

Jul 2008 – Feb 2009

Luiz ‘Big Phil’ Scolari became the first ever World Cup winning manager to coach a Premier League team in the summer of 2008. The charismatic Brazilian came across a jovial figure who even brazenly admitted that his main motivation for joining Chelsea was so he could retire early.

Scolari got his tenure off to a fine start, going unbeaten in his first 12 games and everything seemed rosy in west London. However, results soon began to deteriorate amid reports of his inability to properly grasp the English language and communicate with his players.

With Chelsea in fourth place in the table in February of 2009, the clubs board decided to act and ended Big Phil’s short-lived spell in English Football. He would be replaced in the Stamford Bridge hot-seat by experienced Dutch coach Guus Hiddink, who interestingly enough was managing the Russian national team at the time and on a mega money contract that was being heavily subsidised by a certain Oligarch.

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Roberto Di Matteo

Mar 2012 – Nov 2012

Di Matteo enjoyed a fine spell as a Chelsea player between 1996-2002, back before Stamford Bridge was awash with Russian oil money, and the West London club were seen as a fun side to watch and one that were best avoided in cup competitions.

He returned to the Bridge as part of Andre Villas-Boas’ coaching staff in the summer of 2011, having previously managed MK Dons and West Brom. Former Italy international Di Matteo took over from Villas Boas as manager in March 2012, with Chelsea struggling badly after the young Portuguese coaches methods proved unpopular amongst the Blues squad.

Di Matteo got off to a cracking start, overturning a 3-1 first leg loss to Napoli in the Champions League, before following that up with a famous win over Barcelona in the semi-final of Europe’s most prestigious cup competition.

It wasn’t long before he had his hands on silverware, with the Blues beating Liverpool 2-1 in the FA Cup final. Then came the biggest night in Chelsea’s history when an injury and suspension-ravaged Blues side beat German giants Bayern Munich on penalties in the Champions League final.

Despite the predictable accusations that once again Terry and co. had effectively been self-policing themselves to cover up for a below-par coach, Chelsea had little option but to hand the Italian the managers job on a full-time basis.

However, Chelsea’s form would soon fall off a cliff the following season, and he was given the chop in November after an embarrassing 3-0 loss to Juventus in the Champions League and replaced with the left field option of…

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Rafa Benitez

Nov 2012 – May 2013

In what can only be described as the managerial equivalent of ‘putting a square peg in a round hole,’ Chelsea appointed Benitez as ‘interim manager’ to replace Di Matteo.

On paper, Benitez was one of Europe’s leading coaches having enjoyed successful spells with both Valencia and Liverpool. However, he was despised by the Stamford Bridge faithful due to the bitter rivalry that had developed between Liverpool and Chelsea during the Jose Mourinho era.

Right from the start, this one seemed like a marriage made in hell with Blues fan openly hostile towards Benitez while the Spanish coach was vocal in his distaste for his title of ‘interim manager.’

Despite being ridiculed by his own fans at every game and being labelled a ‘fat Spanish waiter’ Benitez guided Chelsea to a third-place finish in the Premier League and won the Europa League with a 2-1 win over Benfica in Amsterdam. Both parties inevitably parted ways soon after and Benitez still receives a bizarre level of abuse whenever he returns to Stamford Bridge.

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Maurizio Sarri 

Jul 2018 – Jun 2019

A buzz swept throughout Stamford Bridge last summer when Chelsea eventually completed a long-protracted deal with Napoli to bring Maurizio Sarri to the Premier League. Hipsters had been conversing in their secret lairs for a few years previously about this eccentric former Banker who had made his way up through the Italian leagues and had his sides playing a wonderful form of progressive possession-based football.

Then when his Napoli side pushed Juventus all the way in the 2017/18 Serie A title race, the secret was out and everybody agreed – after watching a 2:20 video on twitter – that Sarri-ball was the Dogs Bollocks, and we all couldn’t wait to see it in action in the English top-flight.

Things began well for Sarri, and after an Eden Hazard inspired run of 12 games without defeat in the Premier League, many of us were even tipping the Blues for an unlikely title tilt. However, Chelsea fans soon started to realise that Sarri-ball, for the most part, simply involved quite a lot of sterile possession, while the decision to move the best holding midfielder in world football, N’Golo Kante, out of position to accommodate £57 million summer signing Jorginho became something of a rarity amongst football fans – everybody agreed it was stupid.

Results began to slip and discontent reached epic levels at the Bridge – especially after two humiliating losses, 6-0 to Man City and 4-0 to Bournemouth. However, Maurizio did get the chance to win the first piece of silverware of his career, when Chelsea reached the Carabao cup final against Man City back in February. Then came the most iconic moment of Sarri’s tenure, the Kepa-Arrizabalaga-Saga…

Despite his squad looking like they were simply going through the motions, Chelsea did manage to go on a decent run of form towards the end of the campaign and would eventually finish in a respectable third place in the Premier League. 60-year-old Sarri would then finish his Chelsea career on a positive note, beating London rivals Arsenal 4-1 in the Europa League final and finally get his hands on a winners medal.

With Sarri public enemy number one among his own fans, Eden Hazard leaving for Real Madrid, and the Blues facing a two window transfer ban, the Italian coach wisely decided to take up the offer to become Juventus’ new manager. On paper at least, Sarri enjoyed a relatively successful year in charge, but that doesn’t fully tell the story of a drama-packed managerial reign that only Chelsea seem capable of pulling off.

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Read Also: Football’s Ultimate Shithouse XI


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