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15 Greatest Left-Wingers in Premier League History [Ranked]
The Premier League has witnessed so many exciting wingers over the years. From the fastest players in the competition, to widemen that are full of tricks, to those that have a great end product, you sometimes come across individuals who possess all three of these attributes.
Outstanding wingers have been responsible for dozens of breathtaking moments in the Premier League era. Whether that be a long range goal, a laser-guided cross or pass for an assist, or a skillful dribble in which someone has taken on the entire defence and still managed to score. But, what we want to find out is the greatest left-wingers in Premier League history, and there are a lot of good ones to choose from.
Ranking Factors
- Goals & Assists: We are looking for players with plenty of goals and assists throughout their Premier League career.
- Longevity: How long they competed in the Premier League for.
- Achievements: What did they manage to accomplish in their Premier League career?
- Impact: How much impact did they have on big games? Were they able to produce big moments?
15
Damien Duff
The Chelsea teams of the 2000s were blessed with incredible talent – the likes of Frank Lampard, Didier Drogba, John Terry, Claude Makelele, and so on. They even had a young Arjen Robben on their books, but Damien Dufff was an underrated part of Jose Mourinho’s incredible machine.
Across the two title-winning seasons in 2004/05 and 2005/06, the Republic of Ireland international played in 58 matches, weighing in with 18 goal contributions to help the Blues lift a first English top flight in 50 years. Having also been a consistent threat at Blackburn Rovers prior to that and then Newcastle and Fulham following his stint at Stamford Bridge, the Ballyboden-born winger was capable of playing on either flank, possessing frightening speed which helped him terrorise full-backs.
14
Marcus Rashford
As a fresh-faced 18-year-old, Marcus Rashford was handed his Premier League debut in a huge tie as Manchester United hosted Arsenal. Louis van Gaal showed immense faith in the Carrington graduate, but he passed the test with ease, scoring twice against the Gunners before assisting Ander Herrera to make sure of all three points.
That was to set the tone for much of the England international’s career at Old Trafford. Touted for big things, he wasn’t always consistent and performances sometimes dipped, but he still managed 89 goals and 42 assists over the course of 297 games in the English top flight. Had Rashford managed to win a Premier League, he’d undoubtedly be even higher in this list.
13
Harry Kewell
Coming through the ranks of Leeds United’s academy during the years after the English top flight was rebranded as the Premier League, Harry Kewell was handed a debut against Middlesbrough in March 1996. He quickly became touted as a talented prospect, winning PFA Young Player of the Year during the 1999/00 season as he helped the Whites to a third-place finish.
His performances at Elland Road enticed Liverpool, who parted with £5m to sign him in 2003. The Australian would go on to win a Champions League and FA Cup while at Anfield, but a Premier League ultimately eluded him and the Reds, with him battling through injuries for a large portion of his career on Merseyside. Nevertheless, he still ended his time in the English top flight with 274 appearances, 57 goals and 37 assists.
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12
Alexis Sanchez
During his time at Arsenal, few left-wingers in the Premier League offered the same level of threat as Alexis Sanchez. The Chilean was simply unstoppable when at the peak of his powers, beating defenders for pace before finishing in spectacular fashion.
Arsene Wenger and co. often relied on the former Barcelona star to dig them out of trouble, with his 2014/15 season, where he scored 16 goals, seeing him earn a spot in the PFA Team of the Year. He even went on to better that total in 2016/17, scoring an impressive 24 times and assisting teammates on 10 occasions. Sanchez might well have gone on to become one of Manchester United’s worst signings when he swapped the Emirates for Old Trafford, but his legacy as a Gunner is simply too strong to ignore completely.
11
Leroy Sane
Leroy Sane was absolutely devastating for Manchester City before suffering an ACL injury in the 2019/20 season. He could operate from the left flank or right flank, but on either side, he used his incredible quickness, vision and shooting ability to exploit the opposition.
The German had a rocket of a shot from his left foot, often finishing chances around the edge of the box with a powerful driven shot into the bottom corners. If the shot wasn’t open, he would slide a delicate pass beyond the defensive line through to his teammates to finish off the move.
10
John Barnes
Had we been factoring in a player’s complete career when completing this list, then John Barnes would have been a lot higher. The former Liverpool star won two English First Division titles while at Anfield — but this ranking is strictly to do with Premier League performance.
Consequently, the former England dynamo sits in 10th place, due to some of his best performances coming before the top flight was rebranded. Nevertheless, Barnes was still a phenom during the Premier League’s early years for Liverpool, scoring 22 times for the Reds and a further six times for Newcastle. Hailed by Jamie Carragher as his most technically gifted teammate, the winger’s skill on the ball was unparalleled at the time.
9
Marc Overmars
Marc Overmars was the perfect winger during his prime years; he had explosive pace and dribbling ability to get beyond any defender. He was capable of shooting or crossing with either foot, so he was a defender’s nightmare to come up against, especially when they already had to deal with the brilliance of Thierry Henry and Dennis Bergkamp.
Despite only having three years at Arsenal, racking up 25 goals and 27 assists in a century of appearances, the Dutchman had many highlights, particularly in the 1997/98 campaign, where Arsenal won their first league title since 1991. Overmars managed 12 goals and five assists that campaign, with him an underrated cog in Arsene Wenger’s first full season at the club.
8
David Ginola
The Premier League had some unbelievable talents back in the mid to late 90s, and David Ginola was one of those. The Frenchman had a deft touch and he made some very good defenders look silly during his days at Newcastle United and Tottenham. He often used his excellent dribbling ability to take on two or three players before curling the ball into the far corner from the edge of the box.
While Ginola doesn’t have spectacular numbers or a Premier League title, he produced some magnificent individual moments during his prime years in the top flight. In fact, back in 1999, the great Johan Cruyff even claimed Ginola was the best player in the world.
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7
Gareth Bale
Gareth Bale made his name at Spurs, before joining Real Madrid back in 2013 for a whopping £85.1 million fee. Initially a left-back, the Welshman would be converted to a left-winger by Harry Redknapp when he joined Tottenham back in 2007, and he never looked back.
He was lightening quick, but also had the power to go with it. This allowed him to bomb down the flank, breezing past everybody before applying the finishing touch to a move. Equally, Bale was blessed with supreme shooting technique from distance, which allowed him to pull off outrageous goals from 25+ yards out as well as from free-kick situations. In his first spell at Tottenham Hotspur, Bale totaled 42 league goals. He returned to Spurs on a season-long loan back in September 2020 where he added another 11 to his tally.
6
Son Heung-min
Having joined Tottenham in 2015, Son Heung-min dazzled his opponents for a decade with his burst of pace, quick feet and his ability to deliver crosses or score goals with either foot. He produced a number of big moments throughout his time in England too, scoring 127 goals and providing 71 assists in 333 appearances.
Sharing the 2021/22 Golden Boot with Mohamed Salah, a Premier League title was the only thing missing from the South Korean’s CV in the English top flight, which is crazy to think considering he and Harry Kane combined for hundreds of goals in their many seasons together. Son brought his career in England to a close in August 2025, but left north London has an undisputable Spurs legend.
