Middlesbrough's Will Lankshear - Arsenal and Tottenham Hotspur
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Will Lankshear could soon become a major source of regret for Arsenal and Spurs, with the Middlesbrough striker taking the Championship by storm after leaving north London behind.
The Gunners released him as a teenager, while Tottenham Hotspur eventually allowed him to depart permanently after several loan spells. Now, the 21-year-old is emerging as one of English football's most exciting young centre-forwards, with his goalscoring exploits attracting rave reviews on Teesside.
Given the respective striker situations at Arsenal and Spurs, both clubs could soon find themselves questioning whether they made the right decision. Even though hindsight is a powerful thing, Lankshear is showcasing for Middlesbrough why he has the potential to be an effective Premier League player one day in the near future.
Arsenal and Spurs could regret allowing Will Lankshear to leave
Will Lankshear
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Football is littered with examples of clubs allowing talented youngsters to slip through their fingers, only to watch them flourish elsewhere. Lankshear could be the latest, having already established himself as one of the Championship's most exciting forwards under Kim Hellberg at Middlesbrough.
Arsenal released the striker at just 15, while Spurs subsequently signed him and oversaw his development through several loan spells before sanctioning his departure to Teesside. However, his performances for Boro suggest Tottenham may have given up on him prematurely.
Lankshear did not necessarily adapt quickly to senior football in his first loan, but he has since showcased what he is about. He combines intelligent movement, a powerful frame for his age, natural finishing instincts off both feet, and an impressive understanding of how to operate inside the penalty area already.
He has become a vital component of Hellberg's new-look attack, with the Swedish coach providing an environment in which his strengths can flourish. The attack-minded style of play creates a number of chances and Lankshear regularly gobbles them up, having scored numerous goals via tap-ins or rebounds.
That is not a coincidence, given his poaching instincts and nose for where to be. On top of that, given his age, potential, and immediate impact, Lankshear is already looking like one of Middlesbrough's signings of the summer, as well as one of the best players in the Championship. Arsenal and Spurs, meanwhile, could soon discover just how costly their respective decisions prove to be.
Will Lankshear has already taken the Championship by storm
Will Lankshear Middlesbrough
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Lankshear's goalscoring numbers make for remarkable reading. His brace against Bolton Wanderers on Friday took him to 13 goals for Middlesbrough before November, having scored 12 times in all competitions during his loan spell at Oxford United last season.
Add his goal for England's Under-21s and he has already registered 14 goals across club and international football this campaign. His rise has been particularly impressive given the unconventional nature of his development, too.
Alan Shearer Blackburn Rovers Premiership title x Declan Rice West Ham United UEFA Conference League
Alan Shearer Blackburn Rovers Premiership title x Declan Rice West Ham United UEFA Conference League
In terms of other clubs that might regret their decision, Sheffield United also had Lankshear in their academy before he eventually moved on, meaning they could have their own reasons to wonder what might have been.
For a striker still so early in his career, his ability to translate potential into consistent goalscoring in senior football is hugely encouraging. Not only for Boro, but for England as well. Recent Ballon d'Or winner Harry Kane is 12 years older than Lankshear and the national team need a successor at some stage.
Will Lankshear should be facing Arsenal and Spurs next season
Amario Cozier-Duberry with Will Lankshear of Middlesbrough
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There is a growing possibility that Lankshear will be inflicting further pain on Arsenal and Spurs next season, with Middlesbrough currently leading the Championship table and looking increasingly capable of securing promotion.
Hellberg did a very respectable job in 2025/26, producing some of the division's most impressive football when his ideas clicked. Crucially, Boro now possess a considerably stronger and more balanced squad, after losing Hayden Hackney and Morgan Whittaker.
They look better equipped for promotion than parachute-payment rivals such as Wolves and West Ham, making a return to the Premier League an extremely realistic prospect. Should Middlesbrough go up, Lankshear could find himself facing the two north London clubs that previously allowed him to move on.
Even if Boro fall short, it is difficult to imagine Premier League clubs ignoring a young striker producing these numbers. A top-flight move next summer would be the logical next step if he has ambitions of featuring for England, potentially putting him directly in the path of Arsenal and Spurs. Either way, both clubs could soon be reminded of what they let go.