Can Chilwell become one of Chelsea’s best-ever left-backs?

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Learning from the very best is the ideal scenario.

And new Chelsea left-back Ben Chilwell has a Blues legend at very close hand as he tries to make the role his own following his summer move from Leicester City.


But will the 23-year-old be able to finally solve the problem position of left-back following Ashley Cole’s departure in 2014?

Many have tried, but they are big boots to fill.

The right-footed Cesar Azpilicueta and Marcos Alonso, an attacking player much more suited to a wing-back role, have undoubtedly had their moments and enjoyed great success, but they have not always been convincing.

West London Sport takes a look at a few of the standout performers to have played at left-back for Chelsea since the 1980s.

Joey Jones

A cult hero whose no-nonsense style and passion made him an instant hero at Stamford Bridge. Jones enjoyed league success and European Cup glory with Liverpool and spent three seasons with Chelsea from 1982, initially helping the Blues avoid relegation and then winning the 1983-84 Division Two title.

Tony Dorigo

A wonderful attacking defender who was adored by Chelsea fans in the late 1980s before wanting to leave to further his ambitions. Dorigo’s move to Leeds, where he won the Division One title in his first season, did not endear him to Blues fans. But the England international had pace, a great touch, a glorious left foot and scored many a delightful goal – and generally shone while in a Blues shirt.

Graeme Le Saux

A brilliant winger who shone as a youngster before being rashly sold to Blackburn Rovers where he won a Premier League title playing as a full-back in 1994/95. The huge error was rectified to the tune of £5m in 1997 and Le Saux, another England man, returned to make the left-back role his own until he moved prior to the Roman Abramovich era in 2003.

Wayne Bridge

A fine full-back and the scorer of one of the most memorable goals in Chelsea Champions League history when he hit the winner against Arsenal at Highbury in the 2003-04 season. Bridge made more than 100 appearances for the Blues and was yet another England international left-back, but he lost his place to one of the greatest left-backs this country has ever seen…

Ashley Cole

A Chelsea legend. Cole joined Chelsea in 2006, winning the Premier League in 2010, the Champions League in 2012 and four FA Cups before he joined Roma in 2014. He won 107 caps for England and is now on the club’s coaching staff.

Cesar Azpilicueta

Chelsea’s Mr Dependable has been a regular across every position in the defence since joining in August 2012. A right-back by trade, he helped Chelsea win the title playing out of position at left-back under Jose Mourinho and then arguably found his best position playing in a back three as Chelsea won the title against under Antonio Conte.

Marcos Alonso

If ever there was a player made to play as wing-back it’s Alonso,. The Spaniard has an attacking instinct and eye for goal that many a striker would bed proud of but playing as a left-back, his defensive positioning and a lack of concentration has often seen him heavily criticised when things go wrong at the back.