Leo Castledine, born on 20 August 2005 (age 20), is an English central attacking midfielder with Middlesbrough. He wears the number 23 shirt and is valued at around £1.5m by Transfermarkt.
His senior career is still at an early stage, but it is Middlesbrough that has shaped it so far. Across two seasons he has made 11 appearances in all competitions, scoring one goal, with nine of those outings coming in the Championship and another two in the play-offs.
The 2025-26 season has been his most productive to date, with nine league appearances and one goal. It is a modest body of work, but enough to place him on the fringes of Middlesbrough’s first-team picture rather than in the realm of academy promise alone.
Castledine remains a developing professional whose career is presently centred on Middlesbrough. His next step is straightforward enough: more minutes, more influence, and a clearer role in the side.
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