Leo Castledine: Chelsea star set for permanent exit as Liam Rosenior reign gets underway | OneFootball

Leo Castledine: Chelsea star set for permanent exit as Liam Rosenior reign gets underway | OneFootball

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Evening Standard

·8 January 2026

Leo Castledine: Chelsea star set for permanent exit as Liam Rosenior reign gets underway

Article image:Leo Castledine: Chelsea star set for permanent exit as Liam Rosenior reign gets underway

Former AFC Wimbledon starlet has been playing League One for the last two seasons

Leo Castledine is leaving Chelsea to join Middlesbrough on a permanent deal.


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Standard Sport understands the 20-year-old will sign a long-term contract with Boro, and his medical will be conducted in the north east on Friday.

Chelsea have agreed a sell-on clause to be inserted into the deal.

The midfielder had been impressing while on loan at Huddersfield Town, where he has scored 12 goals and registered five assists this season.

The Huddersfield loan came after a season at Shrewsbury Town, where he started well before suffering a stress fracture in his lower back.

In joining Middlesbrough, he is signing for the club he made his Chelsea debut against in a 6-1 Carabao Cup game in January 2024.

The England youth international is a Chelsea academy graduate but also spent seven years in AFC Wimbledon’s youth system.

Castledine had attracted interest from Watford and Bristol City but is instead joining their Championship rivals Middlesbrough after a deal was struck with Chelsea.

He had a break clause in his Huddersfield contract that has allowed the move, and he was due to be out of contract at Chelsea in the summer.

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