Leo Castledine, born on 20 August 2005 (age 21), is an English central attacking midfielder with Middlesbrough. His senior career to this point is tied closely to Boro, where he wears the number 19 shirt and carries a market value of around £1.5m, according to Transfermarkt.
Middlesbrough is where the substance of his first-team record sits. Across two league seasons he has made 11 league appearances and scored once, with his busiest campaign coming in 2025-26, when he scored one goal in nine league games.
In 2026-27, Castledine has added two Championship appearances, two League Cup appearances and two Championship play-off appearances for Middlesbrough. It remains an early-stage senior career, but the shape of it is clear enough: an attacking midfielder trying to build a proper run at the club where most of his football has been played.
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