New boss: Liam Rosenior has succeeded Enzo Maresca as Chelsea head coach
Chelsea Football Newsletter
The Blues’ former Under-18s and U21s captain has completed a permanent move to Championship promotion contenders Middlesbrough, signing a four-and-a-half year contract on Teeside until the summer of 2030.
It comes after he spent the first half of the season on loan in League One with Huddersfield, where he impressed by scoring 12 goals and registering five assists in 27 appearances before Chelsea exercised their January break clause.
Standard Sport understands that Chelsea agreed a sell-on clause as part of the deal, with Middlesbrough seeing off competition from second-tier rivals Watford and Bristol City for the former England youth international.
Castledine’s switch to the Riverside Stadium ends a six-year stay at Chelsea, where he had been a highly-rated regular at academy level and featured for the U18s and U21s after initially joining their U15s from AFC Wimbledon.
His only senior appearance for the Blues came against new club Middlesbrough, replacing Raheem Sterling for the final stages of a 6-1 victory in the second leg of a Carabao Cup semi-final tie at Stamford Bridge in January 2024.
“Leo Castledine has left Chelsea and completed a permanent transfer to Championship club Middlesbrough,” Chelsea confirmed in a statement.
They added: “We thank Leo for his efforts throughout his time at Chelsea and wish him every success as he embarks on a new chapter in his career.”
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He bolsters Kim Hellberg’s squad for what they hope will be a successful second half to their push for a first return to the Premier League since 2016/17, currently occupying the second automatic promotion slot behind Frank Lampard’s Coventry after 26 matches - six points off the top and two clear of Ipswich, who have a game in hand in third.
Boro bounced back from a four-match winless run by hammering Southampton 4-0 at home last time out, with an FA Cup third-round trip to Fulham on Saturday followed by league games against West Brom, Stoke, Preston and Norwich in January.
"I’m absolutely over the moon to join what is a massive, massive club,” Castledine - who saw a loan at Shrewsbury last term cut short by injury - told Middlesbrough’s official website.
"It’s a really big step for me in my career and I’m very excited to be here.
"There’s always been trust in young players at this club if they can perform, and I want to perform at my highest level.
"I’m fit, healthy and I’ve been playing well, so I feel ready to go. I want to help the team as much as I can from the first day."
Chelsea are also reported to have recalled injured American left-back Caleb Wiley from his loan stint at Watford.