Leo Castledine (born 20 August 2005, age 21) is an English central attacking midfielder whose senior career has so far been shaped almost entirely at Middlesbrough.
He has made 12 league appearances across two seasons for the club, with his most productive league campaign coming in 2025-26, when he scored once in nine appearances. That is still a modest body of work, but it is where his professional profile has been built.
In 2026-27, Castledine has made three Championship appearances, along with three League Cup outings and two in the Championship play-offs for Middlesbrough. Wearing squad number 19, he remains in the first-team picture rather than on its fringes in name only.
His market value is around £1.5m, according to Transfermarkt. At this stage, Castledine’s career is a Middlesbrough story: early, contained, and still being defined by regular senior minutes.
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