Leo Castledine

Shrewsbury Town (loan) On 26 August 2024, Castledine joined League One side Shrewsbury Town on a season-long loan deal. He made his debut for the club the next day on 27 August 2024, in a 2–0 defeat to Bolton Wanderers in the EFL Cup. He scored his first goal for the club on 31 August 2024, in a 3–0 win against Leyton Orient.

Huddersfield Town (loan) On 1 August 2025, he returned to League One, joining Huddersfield Town on a season-long loan. He made his debut for the club on 13 August 2025, in a 2–2 draw with Leicester City in the EFL Cup which Huddersfield won on penalties. He scored his first goal for the club on 26 August 2025, in a 1–1 draw with Sunderland. Having scored five goals in his final month with the club prior to his recall, he was named EFL Young Player of the Month and EFL League One Player of the Month for December 2025.

Middlesbrough On 9 January 2026, Castledine signed for Championship side Middlesbrough on a four-and-a-half year deal for an undisclosed fee, reported to be a little under £1 million. He made his debut for the club on 16 January 2026, in a 3–2 win against West Bromwich Albion. He scored his first goal for the club on 14 March 2026, in a 1–1 draw with Bristol City.

International career Castledine has represented England at under-15, under-17 and under-18 level.

Personal life He is the son of former Wimbledon footballer, and television presenter, Stewart Castledine, as well as former Homes Under the Hammer host Lucy Alexander. Leo has an older sister, Kitty, an actress who currently stars in EastEnders.

Career statistics

Honours Individual EFL League One Player of the Month: December 2025 EFL Young Player of the Month: December 2025