Best Chelsea players: the 11 greatest of all time

The all-time greatest Blues...

We are part of The Trust Project What is it?

We've put together a list of who we reckon are the greatest 11 players of all time to have ever worn the hallowed blue shirt of the Pensioners. 

Note: this isn't a best Chelsea team - the 11 players are simply the best, regardless of position, and in no particular order.

Agree with our selction of Blues? Should Winston Bogarde be in there? Let us know in the comments below.

1. John Terry, 1998-

Say what you like about the current, possibly outgoing, Chelsea skipper – and most people have – you can’t argue with his record.

If this were a popularity contest, the Blues’ most decorated captain and player might not make the top 10, even among the club’s own fans, but few could question the consistency and quality of his defending, his inspirational leadership and, it must be said, underrated distribution skills and goalscoring ability. They’ll miss him when he’s gone.

2. Frank Lampard, 2001-14

An £11 million signing from West Ham, where his time was overshadowed by accusations of nepotism and taunts about his weight, Lampard proved his class and professionalism over 13 trophy-laden seasons at Stamford Bridge. Possessed of a high IQ on and off the field, Lampard was everything a modern midfielder should be, but it was his goalscoring ability that stood out.

He comfortably broke double figures for 10 straight seasons, scoring 20-plus in five of those, and passed Bobby Tambling’s all-time club record in May 2013.

3. Peter Osgood, 1964-74

From amateur legend Vivian Woodward and pre-war stars Hughie Gallacher and Tommy Lawton, to Kerry Dixon in the ’80s and current incumbent Diego Costa, Chelsea’s history is littered with fine centre-forwards, but none were as iconic as the ‘King of Stamford Bridge’, whose statue stands outside the West Stand.

Tall yet skilfil, ‘Ossie’ played a key role in two Chelsea triumphs; scoring in every round on the way to lifting the FA Cup in 1970, and finding the net in both games of the final a year later as the Blues won the European Cup-Winners’ Cup.

4. Didier Drogba, 2004-12, 2014-15

Remarkably similar stats in terms of appearances and goals to Osgood (above) and Bentley (below), the Ivorian enjoyed neither the cult status of the former or gentlemanly reputation of the latter, but won more trophies than the two put together.

Arriving relatively late to the big time at 26, his mix of pace, power and goalscoring ability made Drogba near-unplayable at time during his Blues pomp, and he had a knack for scoring cup-final goals, including the winning penalty in the 2012 Champions League shootout, Chelsea’s finest hour.

5. Roy Bentley, 1948-56

Bristol-born Bentley only moved south from Newcastle on medical advice in a bid to cure a lung problem, and at first struggled to fill the boots of Tommy Lawton. But after finding his home as deep-lying striker, Bentley became the model of consistency, his powerful shot and aerial prowess enabling him to break double figures for eight straight seasons.

Found the net 21 times in the 1954-55 campaign – including twice against rivals Wolves – when he captained Chelsea to their first-ever trophy, the league title. 

6. Gianfranco Zola, 1996-2003

If Ruud Gullit was Chelsea’s most important signing – indeed, the catalyst for them eventually becoming a global superpower – then the Dutchman’s own first signing, on being made player-manager in the summer of 1996, was their most popular.

Zola two FA Cups, a League Cup and a Cup-Winners’ Cup with the Blues but more than that he was a rare combination of genius and gent, loved by his own fans and admired by everybody else’s.

7. Petr Cech, 2004-15

It took some time before Cech was back to his best following the collision with Stephen Hunt in October 2006 that left the Czech keeper with a fractured skull. Before that, he was imperious as Chelsea won back-to-back Premier League titles, breaking several clean-sheet records along the way.

Among the very best of a new generation of stoppers who were equally adept at making saves, dominating their box and using their feet, he won two more Premier League titles and every other major domestic and European trophy going before joining Arsenal in the summer. Just edges out Peter Bonetti.

8. Jimmy Greaves, 1957-61

Better known as a Spurs and England legend, it was for Chelsea whom Greaves was most prolific, scoring at nearly a goal a game in his four seasons – 132 in total for what was largely a struggling First-Division team – before leaving for AC Milan little after his 21st birthday.

One of (Ted) ‘Drake’s Ducklings’, a less successful answer to the Busby Babes, Greaves combined pace and dribbling ability with deadly finishing – a true phenomenon.

9. Ron Harris, 1961-80

When you’re better known for the sobriquet ‘Chopper’ it’s little wonder people question your footballing ability, but as well as being able to dish it out – and boy could he dish it out – Harris was a central defender of no little ability, playing just five shy of 800 games for the Blues, mainly in the top flight.

Having won the League Cup in 1965, Harris led the Blues to FA Cup and Cup-Winners’ Cup victories in 1970 and ’71 respectively. 

10. Peter Sillett, 1953-62

Ashley Cole and Steve Clarke deserve honorable mentions, but as a full-back Sillett had the lot. Described by Stanley Matthews as the best defender he played against and by Roy Bentley as one of the best passers he had ever seen, Sillett also had an eye for goal, only surpassed by John Terry on the list of Chelsea’s dead-eye defenders.

Won the title with the Blues in 1955 and would have won many more than his three England caps were it not for a relaxed approach to the game.

11. Ray Wilkins, 1973-76

Mainly remembered for being made Chelsea captain at just 18, Wilkins was the one bright spot in the gloom of the late ’70s, establishing himself as an England regular despite two relegations with the Blues.

Silky passing and – in these early days, at least – a fair few goals were ‘Butch’s forte and he was in demand among teenyboppers and England’s biggest clubs alike when he joined Manchester United for a then-whopping £800,000 in 1979.

More features every day on