Few – if any – clubs in English football share Manchester United’s tradition when it comes to wingers.
From Ryan Giggs and David Beckham to George Best and Cristiano Ronaldo, Andrei Kanchelskis and Lee Sharpe success at Old Trafford has been built on wide players.
Even those who won less their colleagues such as Steve Coppell and Jesper Olsen are fondly remembered by the fans for their thrilling style.
But over the last two decades, winger has been an increasingly troublesome position for the 20-time champions of England.
Since Ronaldo made his debut against Bolton as a fresh-faced 17-year-old, United have signed 15 wide players for a combined £372million.
The future of Jadon Sancho (left) and Antony (right) hangs in the balance at Old Trafford amid a difficult relationship with Erik ten Hag and serious allegations of assault respectively
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Nani was successful if at times frustrating and the likes of Ashley Young and Antonio Valencia were converted into full-backs and were solid if unspectacular peformers.
Meanwhile, the jury remains out on the likes of Amad Diallo and Facundo Pellistri due to their limited opportunities.
More worryingly for United, the £150m duo of Jadon Sancho and Antony have failed to live up to their price tags and their respective careers at Old Trafford hang in the balance, albeit for different reason.
Here, Mail Sport takes a look at the worst United wingers over the past 20 years.
David Bellion
Bellion and Ronaldo both arrived at United in the summer of 2003 and both played on the wing. That, however, is where the similarities between the two begin and end.
United paid Sunderland a £2million settlement to resolve tapping up allegations, but the Frenchman never lived up to expectations and scored only eight goals in 40 appearance in all competitions.
A loan move to West Ham was similarly underwhelming and Bellion eventually returning to France, signing for Nice in 2006 after spending the previous season on loan at the Ligue 1 club.
David Bellion was hugely underwhelming after joining United in the summer of 2003
Zoran Tosic
The Serbian arrived at Old Trafford in January 2009 for £7m on the back of two league titles with Partizan Belgrade.
Loaned to Cologne a year later after making just five appearances in all competitions, Tosic left United permanently in the summer of 2010 to join CSKA Moscow.
Sir Alex Ferguson reportedly tried to convince him to stay at Old Trafford, but Tosic was determined to leave. Six major trophies in Russia vindicated his decision, but Tosic admits he regret leaving United.
Zoran Tosic (right) joined United from Partizan Belgrade for £7m in 2009 but left permanently 18 months later after making just five appearances in all competitions
‘When I arrived in Manchester I discovered I was not yet ready for that level,’ the former Serbia international told the Daily Record in 2012.
‘I spoke with Sir Alex many times and he kept telling me I had quality and just had to keep working hard.
‘In the end I wasn’t sure I was going to get the chance I felt I deserved so decided to change club. Even now I am always thinking about that moment. Maybe I should have stayed and fought for my place. This was Man United after all.’
Gabriel Obertan
United received a then-world record fee of £80m for Ronaldo in the summer of 2009, which they proceeded to reinvest on Obertan, Antonio Valencia and Michael Owen for a combined outlay of £19m.
As Sir Alex Ferguson never tired of pointing out, this was a time when ‘there was no value in the transfer market’.
A £3m signing from Bordeaux, Obertan certainly lived up to that statement, as he started just of a third of his 27 appearances for United in all competitions and scored just once in two seasons.
Offloaded to Newcastle in the summer of 2011, he managed only 58 Premier League appearances in five seasons at St James’ Park.
Gabriel Obertan (left) signed for United for £3m in the same summer they sold Cristiano Ronaldo to Real Madrid for a then-world record £80m fee
Bebe
Quite what possessed United to part way with £7m to sign Bebe from Vitoria Guimaraes may never become clear, but in a list of bizarre transfers he ranks as probably the most absurd of the lot.
Sir Alex Ferguson admitted he had never seen him play, while his long-time assistant Carlos Queiroz also dismissed any involvement with the deal.
‘Bebe was not even part of our scouting files for the national team of Portugal,’ the Portuguese said in 2014.
‘I knew nothing about him.’
Vitoria Guimaraes had taken a punt on Bebe after he left Estrela da Amadora over unpaid wages in June 2010 and signed him to a five-year deal with a release clause worth north of £2m.
Bebe (middle) was a shock signing as he completed a £7m to United in 2010
Sir Alex Ferguson admitted signing the player without ever seeing him play
But after five goals in six pre-season matches, his release clause was set to £7m amid interest from Benfica and Real Madrid.
The son of immigrants from Cape Verde, who were forced to abandon him as a child, Bebe spent eight years in an orphanage and still lived in the shelter just months before signing for United.
His debut in a League Cup tie away at Scunthorpe – which Ferguson missed because of a scouting trip – came amid much intrigue, but it soon became apparent United were far too big a stage for the Cape Verde international.
Bebe scored just two goals in seven senior appearances across four seasons punctuated by loans to Besiktas, Rio Ave and Benfica before eventually joining the Portuguese giants permanently in the summer of 2014.
Bebe would later admit he ‘never took Manchester United seriously’, but he technically outlasted both Ferguson and David Moyes at Old Trafford.
Wilfried Zaha
United looked to have pulled off a significant coup when they signed Zaha in January 2013 in a deal worth up to £15m, before loaning him immediately back to Crystal Palace.
But instead of being the first piece of the latest Sir Alex Ferguson rebuild, the Ivorian proved to be the Scot’s last ever signing for United.
One of the most promising talents in English football – he was voted the EFL’s Young Player of the Year in 2012 – Zaha looked lost at Old Trafford under David Moyes, starting just two of his four senior appearances for the club.
Loans to Cardiff and Palace followed, before he made his return to Selhurst Park permanent in February 2015.
Wilfried Zaha (right) made just four senior appearances from United after signing from Crystal Palace in 2013 and returned to south London two years later
Angel Di Maria
If most of Di Maria’s predecessors at Old Trafford were complete gambles, the Argentine was the real deal.
Or so United hoped, as they forked out £59.7m to sign him from Real Madrid for what was then a British transfer record.
A multiple Champions League winner, Di Maria had seemingly all it took to make the No 7 shirt his own and hit the ground running with two goals and two assists in his first four Premier League games.
Angel Di Maria signed for United in a then-club record £59.7m deal from Real Madrid
But that was as good as it got for the Argentinian, whose form nosedived after playing just 59 minutes in seven matches over a four-month spell.
Di Maria claimed his issues stemmed from Louis Van Gaal’s iron-fisted approach.
‘I would score, assist and the next day he would show me my misplaced passes,’ the former Real Madrid star told Argentine outlet Tyc Sports.
‘He displaced me from one day to the other, he didn’t like players being more than him.’
The Dutchman, unsurprisingly, had a different opinion: ‘He never convinced me in any of those positions,’ he told the BBC.
The Argentine never settled in Manchester, was not happy with Louis Van Gaal and was sold to Paris Saint-Germain after just one season in England
‘He could not deal with the continuous pressure on the ball in the Premier League. That was his problem.
Di Maria’s lack of form on the pitch was exacerbated by failing to settle in Manchester, with his wife Jorgelina Cardoso describing the country as a ‘s***hole’.
Unsurprisingly, a year later he packed his bags and headed to PSG.
Memphis Depay
Much like Di Maria, Depay arrived at United surrounded by big expectations following his £25m move from PSV Eindhoven in the summer of 2015.
Much like Di Maria, he was handed the No 7 shirt, flattered to deceive and was ultimately majorly disappointing.
The Dutchman scored seven goals in 53 appearances in all competitions and featured in just eight games in his second season at United, before being offloaded to Lyon in January 2017.
Memphis Depay never lived up to his potential after a £25m move from PSV Eindhoven
Daniel James
James scored on his debut for United as they trounced Chelsea 4-0 on the opening day of the 2019-20 season and followed it up with two more goals in the next three games.
United appeared to have unearthed a gem, but that was as good as it got for the Welshman, who had signed from Swansea in a £15m deal having been labelled as the heir to Gareth Bale.
The jet-heeled winger started 18 of his 26 appearances in his second season at United and departed with nine goals and nine assists to his name in 74 matches.
He signed for Leeds for £30m in the summer of 2021, in a rare case of United selling a squad player for a decent fee.
Daniel James scored on his debut for United as they trounced Chelsea 4-0 on the opening day of the 2019-20 season, but was sold to Leeds two years later
Jadon Sancho
Having spent a year chasing Sancho, United and Ole Gunnar Solskjaer finally got their man for £73m in the summer of 2021.
But the Norwegian, who signed a three-year extension just three weeks after Sancho’s arrival, was gone within four months and Sancho has never hit the heights he reached at Borussia Dortmund.
A meagre return of just 12 goals and six assists in 82 appearances in all competitions has been exacerbated by problems off the field.
Last season, the 23-year-old missed over four months to deal with physical and mental challenges and it has since emerged United were not cleared to go public with the information.
Earlier this month, left Sancho out of the United squad for the trip to Arsenal ‘on his performances in training’.
It prompted a furious response from the England international, who dismissed the claims as ‘completely untrue’ and insisted he has been made a ‘scapegoat’ in a lengthy social media post.
His future at Old Trafford hangs in the balance.
Jadon Sancho has scored 12 goals and provided six assists in 82 appearances for United
Antony
United looked to have finally solved their winger conundrum as the Brazilian scored three goals in his first three Premier League matches after signing from Ajax.
That flying start soon petered out and Antony has done little to justify the £85m fee United paid for him – which makes him the third most expensive signing in club’s history after Paul Pogba and Romelu Lukaku.
The Brazilian’s debut season returned just seven goals and three assists in all competitions, hardly an impressive return.
Erik ten Hag has defiantly kept faith in Ajax protege, who has been placed on leave by the club until further notice following allegations that he attacked three women.
Antony has given TV interviews and publishing WhatsApp screenshots on Instagram as he fights to clear his name. The allegations remain under investigation by police in Manchester and Sao Paulo.
Antony has failed to live up to his £85m fee since joining from Ajax last summer