Softfootball understands that Middlesbrough have secured the permanent signing of Chelsea midfielder Leo Castledine, in what is being hailed as a significant transfer coup for the Championship club.
The deal, finalised today, comes after Castledine’s impressive loan spell at Huddersfield Town and marks the first major transfer decision under Chelsea’s newly appointed head coach, Liam Rosenior.
According to transfer expert Fabrizio Romano via his official X account, the deal is now complete.
He posted:
More details on Leo Castledine to Middlesbrough exclusive story. Chelsea will receive £2m fixed fee plus big sell-on clause included as part of the deal for future profit. Boro have counter-signed all documents.
Chelsea will receive a £2 million fee for the 20-year-old. The deal also includes a notable sell-on clause, ensuring Chelsea, who recently lost 2-1 to Fulham in their last Premier League clash, could benefit financially should Middlesbrough make a profit from any future sale.
This structure reflects the player’s rising profile after a strong loan campaign. During his time at Huddersfield, Castledine impressed, scoring 12 goals and assisting 5 more in 27 appearances across all competitions. Operating mainly as an attacking midfielder, his creativity and hunger for goals quickly made him a fan favourite.
Interest from several Championship clubs followed, but Middlesbrough moved quickly to secure his services. Being under 21, Castledine’s registration won’t count towards Middlesbrough’s 25-man squad limit, giving the club additional tactical flexibility.
Castledine is expected to travel to Teesside soon to complete personal terms and undergo a medical before officially joining Kim Hellberg’s squad.
He is set to sign a four-and-a-half-year deal, signalling Middlesbrough’s long-term plans. His arrival could also open the door for more January signings, with the club also linked to Brighton’s Jeremy Sarmiento.
