Leo Castledine could be playing Premier League football with Middlesbrough next season(Image credit: Getty Images)Copy linkFacebookXPinterestEmailShare this article0Join the conversationFollow usAdd us as a preferred source on GoogleNewsletterFour Four TwoGet the FourFourTwo NewsletterThe best features, fun and footballing quizzes, straight to your inbox every week.Become a Member in Seconds Unlock instant access to exclusive member features.Contact me with news and offers from other Future brandsReceive email from us on behalf of our trusted partners or sponsorsBy submitting your information you agree to the Terms & Conditions and Privacy Policy and are aged 16 or over.You are now subscribedYour newsletter sign-up was successfulWant to add more newsletters?Five times a weekFourFourTwo DailyFantastic football content straight to your inbox! From the latest transfer news, quizzes, videos, features and interviews with the biggest names in the game, plus lots more.Signup +Once a week...And its LIVE!Sign up to our FREE live football newsletter, tracking all of the biggest games available to watch on the device of your choice. Never miss a kick-off!Signup +Join the clubGet full access to premium articles, exclusive features and a growing list of member rewards.Explore An account already exists for this email address, please log in.Subscribe to our newsletterMaking the step from an elite Premier League academy into that club's first team can be a tough transition, and sometimes the best thing a player can do is take a move away to kickstart their career.That's exactly what Leo Castledine has done. After starting out in the academy at his dad's former club Wimbledon, the attacking midfielder made the move to Chelsea.A loan spell with League One Shrewsbury last season was hampered by the side's poor form and ended by injury, but Castledine so thoroughly excelled at Huddersfield in the first half of this campaign that Championship Middlesbrough snapped him up on a permanent move in the January transfer window.You may likeThis is what I've dreamt of since I was a little boy, hopefully I can keep pushing on Lewis Miley could be the man Newcastle Uniteds midfield needs to sink Sunderland and turn the teams disappointing draws into season-defining winsChelsea transfer target dubbed 'the Dutch Pedri' urged to join Newcastle United in January transfer instead'The Boy's A Bit Special' Why the Bukayo Saka regen that Arsenal fumbled is destined for BIG thingsSo who exactly is Leo Castledine?PROFILEName: Leo CastledinePosition/s: Attacking midfielderAge: 20 (Born: August 20, 2005)Nationality: EnglishHeight: 1.79m (5ft 10in)Preferred Foot: RightCurrent Club: MiddlesbroughThe 20 year old became something of a lower-league Frank Lampard for Huddersfield, netting 12 goals in 27 appearances in all competitions - many of them spectacular. That earned Castledine a reputation as a one-man club goal of the season competition (or at least, he would be, if Terriers teammate Ryan Ledson hadn't scored from his own half just after Castledine's departure).Huddersfield were understandably keen to make Castledine's move permanent, but were thwarted by his desire to play at the top end of the Championship with a view to testing himself at a higher level before earning promotion to the Premier League. Middlesbrough fit the bill perfectly.Castledine's strengthsShooting range and technique: Castledine is capable of curling the ball home in almost any scenario both from dead balls and from open play. He banged in a brilliant volley against Sunderland in the League Cup, a postage stamp of a free kick against Luton, and was a constant threat around the edge of the opposition box.Clutch mentality: Huddersfield have not been the most consistent side this season, but they were able to count on Castledine to get them an important goal even when games weren't going their way. Castledine is not the kind of player who only ever adds the third or fourth goal in a rout: four of his 12 goals were equalisers, and five of them put his side into the lead.Get FourFourTwo NewsletterThe best features, fun and footballing quizzes, straight to your inbox every week.Contact me with news and offers from other Future brandsReceive email from us on behalf of our trusted partners or sponsorsBy submitting your information you agree to the Terms & Conditions and Privacy Policy and are aged 16 or over.Arriving into the box: Not all of those goals were worldies, though; there were also plenty where Castledine was able to find the net because he made a run or executed a bit of interplay that got him into exactly the right position at exactly the right time.Consistency: At first glance it looks like Castledine might be a bit streaky, but it's worth keeping in mind that he was in and out of the side in (by League One standards) a very deep Huddersfield squad. But take out his appearances from the bench, and you're left with those 12 goals spread across 19 starts - a phenomenal record for a midfielder.Versatility: Castledine most often featured as one of a pair of 10s behind a centre-forward, but while there are pacier players out there, he has enough tricks in his bag to play out wide too. When required, Castledine has midfield four in a 4-4-2 or on the left of a front three. As long as he's in a role where he has the freedom to come to the edge of the opposition box, he's absolutely fine.What a VOLLEY from Chelsea loanee Leo Castledine for Huddersfield against Sunderland! pic.twitter.com/nR1stIC5GXAugust 26, 2025Castledine's areas of developmentTHAT IS SENSATIONAL! | ALL THE ANGLES | LUTON TOWN vs HUDDERSFIELD TOWN - YouTubeWatch On Stamina: It's partly because of his excellent work rate, but Castledine has often been visibly exhausted late on in games and has had to be subbed off when in an ideal world his side has needed him on the pitch. To date, Castledine has completed the full 90 minutes just nine times across his 56 senior appearances for Shrewsbury, Huddersfield and Middlesbrough. Getting his stamina up, or simply learn to pick his runs more advisedly, would help him to stay on the pitch longer.Defending the flanks: As former centre-back when he was very young, Castledine is decent in the air and a willing and capable presser of the ball in the number 10 role - but he did get exposed by tricky wingers going outside him on a few occasions when he was asked to play out wide in a 4-4-2. Managers who want to make use of his ability to play in wide positions may want him to tighten that up, particularly if Middlesbrough make it into the Premier League.Adding assists to the goals: It's a minor point if he's getting on the scoresheet, of course, but there is room for Castledine to add an extra dimension to his game and keep defenders guessing as he moves up the levels. (Some outlets credit Castledine with five assists at Huddersfield, but that's incorrect; it's actually two, as one of them was him being fouled for a penalty, one was a cross for an own goal, and another is mistakenly credited as his pass when in fact it was a blocked shot.)TOPICSHuddersfield TownChelseaMiddlesbroughChampionshipLeague OneSteven ChickenSocial Links NavigationSteven Chicken has been working as a football writer since 2009, taking in stints with Football365 and the Huddersfield Examiner. Steven still covers Huddersfield Town home and away for his own publication,WeAreTerriers.com. Steven is a two-time nominee for Regional Journalist of the Year at the prestigious British Sports Journalism Awards, making the shortlist in 2020 and 2023.
