9 Best Chelsea Wingers of All-time
- Think Football Ideas
- 15 hours ago
- 6 min read
While we often celebrate strikers and midfield maestros for their goals and creativity, Chelsea FC has consistently thrived on the impact of its wingers, a line of players who have blended technique, vision, and daring pace to shape matches.
Tracing from the audacious runs that stretched defences to the clever interplay that unlocked tight games, the West London club’s history is marked by wide players capable of defining seasons and inspiring moments.
Across eras, these wingers have carried both responsibility and freedom, making fans at Stamford Bridge marvel at their artistry and cementing their place among Chelsea’s most influential figures.
Here Are The 9 Best Chelsea Wingers of All-time
9. Jesper Grønkjær
Jesper Grønkjær’s Chelsea career blended artistry with decisive influence. Arriving from Ajax in 2000 as Denmark’s most expensive player, his flair and pace made him a constant threat as a supporting striker and a winger.
The highlight came on the final day of the 2002/03 season when his curling strike against Liverpool, the famed “billion-pound goal,” secured Champions League qualification and paved the way for Roman Abramovich’s takeover.
Beyond that moment, Grønkjær produced flashes of brilliance in Europe and domestic competitions, his creativity and directness adding a rare edge. Though inconsistent, his legacy endures as one of Chelsea’s most gifted and inventive left wingers.
8. Victor Moses
Victor Moses’ journey at Chelsea tells the story of reinvention and resilience. Signed from Wigan Athletic in 2012, he brought an edge of unpredictability and flair to the flanks, scoring in every major competition during his debut campaign - from the League Cup to the Europa League, which the Blues lifted that year.
Though his early years featured a carousel of loan spells, it was under Antonio Conte that his story took an extraordinary turn. Reimagined as a right wing-back in the Italian’s 3-4-3 system, Moses became one of the pillars of Chelsea’s 2016–17 Premier League title triumph.
His relentless energy, tactical intelligence, and attacking bursts from deep reshaped the team’s rhythm, making him one of the league’s most effective transitional players. Beyond the medals and moments, Moses’ Chelsea spell stands as proof that adaptability can carve a player’s legacy just as sharply as natural flair.
7. Florent Malouda
Florent Malouda arrived at Stamford Bridge in the summer of 2007, stepping into a Chelsea side packed with ambition and heavy expectations. Over the next few seasons, he became one of the club’s most polished and intelligent wide players - a proper winger who combined drive with discipline.
His runs down the left flank were purposeful, often stretching defences and creating openings for the likes of Didier Drogba and Frank Lampard.
Across his Chelsea Premier League career, Malouda made 123 appearances, scoring 33 goals, providing 17 assists, and completing 4,812 passes with an 84% success rate, reflecting both his consistency and technical ability.
Under Carlo Ancelotti, Malouda’s game matured further as he evolved from a traditional winger into a more complete forward, capable of influencing play centrally and contributing consistently to goals.
The 2009/10 campaign became his masterpiece, and a season of double-digit goals, assists, and decisive moments that helped Chelsea claim both the Premier League and FA Cup.
While others sought the spotlight, Malouda’s excellence was often understated, his calm efficiency embodying the balance of flair and reliability that defined that golden Chelsea era. By the time he lifted the Champions League trophy in 2012, his name was firmly etched among the club’s best on the left wing.
6. Willian (2013–2020)
Few players embodied consistency and flair at Stamford Bridge quite like Willian. Signed from Anzhi Makhachkala in 2013, his arrival sparked headlines after a last-minute turn from a rival London club, but it was Chelsea who ultimately benefited from his brilliance.
Over seven seasons, the Brazilian became a fixture on the left flank, balancing tireless work rate with creative poise. Well-versed in his curling free-kicks, sharp acceleration, and knack for decisive goals, Willian was often the difference in tight contests.
He lifted two Premier League titles, an FA Cup, and a Europa League, evolving from a clever dribbler into one of the side’s most reliable performers through managerial upheavals and squad rebuilds.
His professionalism and longevity earned him admiration from teammates and fans alike, while his 2015–16 campaign, where he swept both the Players’ and Fans’ Player of the Year awards, cemented his legacy as one of Chelsea’s finest wide men of the modern era.
5. Joe Cole
Few players embodied Chelsea’s early 2000s transformation like Joe Cole. Arriving from West Ham in 2003 amid the dawn of the Abramovich era, he represented both artistry and audacity — a footballer who played with imagination in an increasingly pragmatic age.
Cole’s flair thrived under José Mourinho, where his blend of tight control, spatial awareness, and improvisation gave Chelsea a rare incisive edge. He became the spark in a team built on discipline, scoring vital goals in title-defining moments and earning the trust of one of football’s most demanding managers.
Injuries interrupted his rhythm, but at his best, Cole was the heartbeat of Stamford Bridge’s attacking play, unpredictable, brave, and technically gifted.
Across seven years, he collected three Premier League titles, two FA Cups, and a League Cup, leaving behind a legacy of a winger who brought flair to a system famed for its efficiency.
4. Pat Nevin
Pat Nevin brought artistry and intelligence to Chelsea’s left wing after arriving from Clyde in 1983. Quick, imaginative, and technically assured, he became a penetrative heartbeat in John Neal’s side, helping secure promotion as Second Division champions while earning Player of the Year honours.
His ability to glide past defenders and create for teammates like Kerry Dixon and David Speedie made him a fan favourite. In the top flight, Nevin delivered in defining moments - from an equaliser at Anfield to vital goals in Chelsea’s 1985–86 title push.
Even as results fluctuated, his flair and composure embodied a purer form of football, securing his place among the club’s most gifted wingers.
3. Damien Duff
Damien Duff’s arrival at Chelsea in 2003 marked the beginning of a new era, both for the club and for the Irish winger himself. Signed from Blackburn Rovers during the early days of Roman Abramovich’s ownership, Duff embodied the ambition of a side intent on reshaping English football.
Quick, technically gifted, and unrelenting in his work rate, he brought balance and unpredictability to Chelsea’s attack.
In his debut season, he became a pivotal figure under Claudio Ranieri, driving the team to their highest league finish in nearly half a century.
When José Mourinho took over the following year, Duff’s adaptability came to the fore. Forming a thrilling partnership with Arjen Robben on opposite flanks, the pair tormented defenders across Europe and the Premier League alike.
His goal against Barcelona in the Champions League and his semi-final winner versus Manchester United in the League Cup became defining moments of Chelsea’s rise.
As the club lifted back-to-back Premier League titles, Duff continued to contribute goals and assists. His influence is a cornerstone of modern Chelsea's identity, making him one of the best wingers the Blues have ever had.
2. Arjen Robben
Arjen Robben’s spell at Chelsea, though brief, left an enduring mark on the club’s left wing. Arriving from PSV Eindhoven in 2004, he combined blistering pace, deft dribbling, and clinical finishing to transform Chelsea’s attack under José Mourinho.
Despite early injuries delaying his debut, Robben quickly became pivotal, contributing to the Blues’ first league title in 50 years and earning Premier League Player of the Month.
His interplay with Didier Drogba and Frank Lampard added unpredictability, while his ability to cut inside and score with precision made him a constant threat.
Even amid recurring injuries, Robben’s skill and determination defined Chelsea’s early 2000s dominance, leaving supporters with lasting memories before his move to Real Madrid in 2007.
1. Eden Hazard
Eden Hazard arrived at Chelsea from Lille in 2012, immediately asserting himself as an incisive force on the left flank. His vision, balance, and close control transformed Chelsea’s attack, allowing him to glide past defenders with an ease that combined flair and precision.
Hazard’s debut season saw him rapidly integrate into the squad, providing key assists, scoring decisive goals, and helping secure early silverware.
Over the years, he became a cornerstone of Chelsea’s Premier League successes, consistently influencing matches with his dribbling, tactical intelligence, and ability to perform under pressure.
Hazard’s left-footed mastery, aerial awareness, and knack for clutch moments elevated him beyond mere statistics, earning him multiple individual awards and a reputation as one of the most complete wingers in the club’s history.
His seven-year tenure at Stamford Bridge left an everlasting mark, blending artistry and efficiency in a way that few players have achieved, making him a natural choice among Chelsea’s greatest left-sided attackers.
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