Ranked! The 10 best Chelsea sides ever

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Few teams have shaped the Premier League more than Chelsea. Tactically they’ve helped change the English game. Narratively, they’ve even won the games that clinched Leicester City and Liverpool their titles. They’re ever-presents: White Walkers, never far from conquering all in their wake with unemotional dreams of domination and a piercing blue stare.

You see, the Blues don’t have the reputation of being revolutionaries - but that’s exactly what they are. Mourinho was the first manager to really bring the 4-3-3 to England, while later, Conte was the first to win big with a three-at-the-back system; Chelsea, for so long, were the big influence for how to judge a prospective club owner and we owe plenty of our modern hire-and-fire culture to the way that Abramovich conducted business. 

Make no mistake, Chelsea have had sides to rank alongside some of the greatest in history, despite their Russian windfall coming as recently as 2003. But which is the greatest Stamford Bridge team that the world has ever seen?

Note: For most of these sides, we're simply looking at one season that defined them, though others were defined by a longer period of time - perhaps they kept winning across that period or didn't have so much change over a few years.

10. 1988/89


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The Chelsea of the late 1980s was unrecognisable to the Chelsea of today. Ken Bates bought the Blues in 1982 and for the majority of the decade, he presided over a yo-yo club, bouncing between the First and Second Division.

By 1989, London was on top. Arsenal were to triumph in the top tier, while Chelsea brought an end to their rollercoaster decade with an emphatic title-winning season. So yes, the 1989 Stamford Bridge heroes are the only team on this list not to play top-flight football - but the manner with which they won promotion makes them deserving of a place in Blues history.

Chelsea won the Second Division title ahead of Manchester City by 17 points. After failing to win their first six games, they dominated the rest of the season, becoming one of the standout second-tier sides in modern history. Tony Dorigo, Dave Beasant and Kerry Dixon were all cornerstones.

Considering how much Chelsea sides have since achieved, it’s easy to play down the crowning glory of a Division 2-winning team. But this was one that laid the groundwork for Chelsea’s 1990s stars and one that lit up their respective competition as much as any Chelsea side has ever done. 

9. 1996/97


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Long before Roman Abramovich had arrived, Chelsea had previous on shelling out on stars. World-renowned players Mark Hughes and Ruud Gullit had both been signed by Glenn Hoddle, before Hoddle left to manage England. Gullit stepped up to player-manage.

It was then that the Blues flirted with the Azurri for the first time. Italian stars Gianluca Vialli, Gianfranco Zola and Roberto Di Matteo swapped Serie A for Stamford Bridge, adding flair to an ever-changing Premier League scene. Chelsea would still lean on the British core of Steve Clarke, Dennis Wise and Scott Minto, but more and more, this was becoming a club open to exports. 

Chelsea lifted the FA Cup in 1997, their first major trophy since the early 70s. Following this up with the League Cup the following year, this side became the springboard for the Blues to launch assaults at the top of the table, eventually pushing the United/Arsenal duopoly of the league into a top-four with them and Liverpool. 

8. 2011/12


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It’s strange that Chelsea’s Champions League-clinching side - arguably the team that reached the pinnacle of Roman Abramovich’s era - is nowhere near the best Blues side ever.

This was a team in disarray domestically that would finish sixth in the league, following a midseason sacking of Andre Villas-Boas. Yet it was the leaders in this team, the spine of Petr Cech, John Terry, Frank Lampard and Didier Drogba, who dragged Chelsea to their first Champions League trophy with knockout wins against Napoli, Benfica, Barcelona and Bayern Munich in their own back yard.

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Arguably no one in this team was in his peak, bar perhaps Juan Mata. It was a low-output season for Drogba with Daniel Sturridge top-scoring in the league; while many of the players in this squad, like Oriel Romeu, Ryan Bertrand and Romelu Lukaku would go on to be bigger figures in other sides.

This Chelsea side had the big occasion down to a tee though, winning the FA Cup to boot that May. In terms of bottle, this Blues side was maybe the best - there was no betting against them in any big game against any opponent, as proven in that extraordinary penalty shootout in Germany.

7. 1954/55


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Ted Drake was a modern kind of manager - for the ‘50s at least. He didn't have the long-coat-and-hat look of a Victorian gentleman: Drake would don a tracksuit and shake hands with the lads before the game kicked off to wish them luck. Chelsea’s old “pensioner” badge changed into a lion. 

And Drake’s Chelsea were a typically strange watch to begin with. The manager had moved for lower league stars that he felt would give their all, rather than the unpredictable primadonnas of the top tier. He would urge the Stamford Bridge faithful to be a bit more passionate and curiously, he insisted that training would be on ball-work - it would never catch on, surely. 

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Chelsea’s 50th anniversary came along in 1955, coinciding with 20 years of consecutive top-flight football. After a 19th-placed finish in Drake's first season, fans probably wondered if they’d have a 21st term in the big time - instead, however, the Blues marched towards a triumphant title. 

Wolverhampton Wanderers were the team to beat. Chelsea’s first-ever league win hinged on them beating Wolves 4-3 at Molineux - after being 3-2 down in stoppage time - before beating them 1-0 at home with a penalty following Billy Wright punching a ball over the bar. It was a dramatic, unexpected and joyful time to be a Blue - Drake was right to encourage more excitement from his fans. 

6. 2020/21


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Thomas Tuchel achieved at Chelsea what he'd been hired to do at Paris Saint-Germain, to a tee. Organise a bunch of expensive yet exciting big-money stars bought by the ownership into one cohesive machine, with Thiago Silva to guide them to European glory.

And though it wasn't often pretty watching Chelsea's second European champions, boy was efficient. They barely conceded. The well-oiled cogs of Kovacic, Jorginho and Kante kept the engine ticking while a rotating cast around them provided the sparks of pure genius. Yet this didn't feel like a finished product but simply a brilliant manager's answer on how to get the best from a ragtag group he'd inherited.

So why's this team so low in our ranking? Well, despite incredible performances along the route to glory, the achievement belongs mostly to Tuchel. They almost threw away Champions League qualification for the following season and an FA Cup defeat to Leicester City tainted just how formidable this set of players was. An unbelievable team – seriously, one of the most impressive in recent seasons – but Chelsea have a few better…

5. 2016/17


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A 3-0 defeat to Arsenal, in which Chelsea switched to a back three mid-game, is seen as the birth of Antonio Conte’s title-winning machine. Really, it was the 3-1 victory away to Manchester City against newly-installed Pep Guardiola that confirmed that this was a system that could win trophies. 

Conte had toyed with three at the back in other jobs but this was when the Italian really nailed his colours to the potentials of wing-backs, liberos and a ferocious counter-attack that the rest of the league couldn’t deal with. That afternoon at the Etihad, Pep’s side bombarded Chelsea with wave after wave of attack. They were undone by swift efficiency of reply.

The genius of this team was that it was built from the ashes of Jose Mourinho flying too close to the sun. Leftovers of Mourinho’s dismal title defence were reborn; Moses and Alonso became marauding wide-men, Fabregas moved higher, Hazard was given a free role unshackled by defensive responsibility and N’Golo Kante joined, winning a second title in a row with his unbridled, motoring midfield presence.

For the first time, a Premier League side won the trophy with a back three. Conte never did build on this foundation effectively - but for a season at least, they were unplayable.

4. 2014/15


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Jose Mourinho’s second coming felt like his final chapter. This felt like Ross and Rachel finally getting together; Mourinho talking about settling down and staying, Abramovich burying the hatchet. It felt like the right place, the right time, for Jose and Chelsea to pick up where they left off. For a while, they did.

In Mourinho’s sophomore season, no one could lay a glove on him. He’d brought Thibault Courtois, Cesc Fabregas, Diego Costa and Nemanja Matic into the side and they all made an instant impact. Chelsea were miles ahead of the pack by Christmas and not just by squeezing 1-0s here and there - Eden Hazard was scintillating, Oscar and Willian in top form and Fabregas was rolling back the years in this team. Diego Costa was a soap villain of a striker; bullying, demeaning and belittling the opposition in a way that no one has done since for Chelsea.

What happened next was a burnout that not even the biggest Mourinho sceptic could possibly have foreseen. Again, the odd couple divorced; Roman moved onto another Italian fling while Mourinho shacked up with a bitter enemy. But when it was good, the good times were great.

3. 1970 - 1972


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Chelsea were hard-working and gritty in the 1950s; they were glamorous and cool in the 1960s. At the start of the ‘70s, the two halves of this one club came together for an exquisite golden age. 

With manager Tommy Doherty sacked for locking horns with half the dressing room, the more serene figure of Dave Sexton was drafted in to cool things down. He brought in a brand-new central-defensive partnership of Webb and Dempsey but the chassis of the side remained untouched. The Blues looked to evolution rather a revolution.

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Leeds United were the top dogs by 1970 and Chelsea managed to knock them off their perch in the FA Cup final, which went to a replay. This was a Blues side who had goals in them, thanks to Peter Osgood and Ian Hutchinson up front - they could keep Sexton’s side in any game and flick on the switch to turn the tide. This was a team of style, sure, but they had considerable steel.

Chelsea’s Cup triumph qualified them for the Cup Winners’ Cup. Another final replay brought another trophy - against Real Madrid, no less. Though league success was limited, this became the standard that a generation of Blues fans expected from their club.

2. 2009/10


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The post-Mourinho years in West London were rocky. This was Sir Alex Ferguson’s renaissance, Arsenal and Liverpool were still title contenders and the likes of Tottenham Hotspur and Manchester City were beginning to lay foundations. Amidst all of this, Carlo Ancelotti delivered one of his most vintage teams.

Across the pitch, Mourinho’s heroes had matured into world-class footballers. Cole, Terry and Ivanovic were all arguably the best in the world at their roles. Drogba was about to hit an unprecedented 29-goal haul, the back-up option was a supercharged Nicolas Anelka, and the midfield options included Lampard, Essien, Ballack and Mikel. The depth was ludicrous, let alone the first team.

Carlo Ancelotti

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Four times, Chelsea scored seven or more goals in a league game. They conceded one goal en route to the FA Cup. They beat Arsenal, Liverpool and United home and away. And the best thing for Chelsea fans? These players loved playing for Ancelotti. They adored the manager and would never give less than everything for the cause.

The Blues still talk highly of Don Carlo. He may not have been at the Bridge long but with this all-conquering side, he most certainly left an impression.

1. 2004 - 2006


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Jose Mourinho’s first Chelsea side is perhaps the greatest Premier League side ever - maybe one of the all-time great club teams. The ridiculously low total of 15 goals conceded is often talked about - as is the fact that Jose never lost a home league game in his first Chelsea tenure - but it’s sometimes forgotten just how well-rounded this team were. 

They weren’t just a defensive unit: Chelsea only scored one fewer goal than the Invincibles when they won the title in 2005 and 2006 - the first title, they’d only lost one more game than them, too. Jose’s men won a League Cup too in that first season and were only beaten in the Champions League by Liverpool and Luis Garcia’s highly-controversial ghost goal. They were a formidable attacking team with a young Arjen Robben, Damien Duff and Joe Cole to choose from.

Petr Cech, Frank Lampard, Jose Mourinho and John Terry at Chelsea with the Premier League trophy

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Chelsea didn’t just shut out teams, they destroyed them too. The Premier League had rarely seen midfield battles like it, with Mourinho flooding the key areas and creating numerical superiority. It was from this side that the idea of Chelsea being ruthless fighters came from: this was a team that had an identity so strong, that it carried each of the players onto great things up until their own respective exits from the Bridge.

It’s always hard to top your first masterpiece and perhaps Roman Abramovich will never quite see a first season like the one when he brought the Special One to England. This is the gold standard and not just for Chelsea teams - it’s a bar to judge all English champions by.

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Mark White
Staff Writer

Mark White has been a staff writer on FourFourTwo since joining in January 2020, writing pieces for both online and the magazine. An encyclopedia of football shirts and boots knowledge – both past and present – Mark has also been to the FA Cup and League Cup finals for FFT and has written pieces for the mag ranging on subjects from Bobby Robson's season at Barcelona to Robinho's career. He once saw Tyrone Mings at a petrol station in Bournemouth but felt far too short to ask for a photo.