Liam Rosenior gives green light to first Chelsea transfer as new era begins

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Chelsea starlet Leo Castledine is on the verge of leaving the west London club on a permanent basis after impressing while on loan at Huddersfield Town this season

Leo Castledine is set to join Middlesbrough from Chelsea on a permanent deal, football.london understands.

The 20-year-old has been in superb form on loan at Huddersfield Town this season, where he has scored 12 goals and recorded five assists across the course of the campaign. Boro have been impressed by the form of Chelsea's academy starlet and have now agreed a deal to sign him permanently, with Castledine set to undergo his medical in the north east on Friday.

Chelsea are set to receive a fee close to £2million for Castledine with the west Londoners inserting a sell-on clause in his contract at the Riverside. Castledine joined the Blues initially at the age of five before moving to AFC Wimbledon two years later. But in 2020, Chelsea re-signed Castledine before signing his first professional contract at Stamford Bridge in August 2022.

Castledine made his first-team debut for Chelsea in a 6-1 Carabao Cup semi-final victory over Middlesbrough in January 2024. That, though, was the only time Castledine appeared for the Blues' senior side.

It is set to be the first transfer sanctioned in Liam Rosenior's reign as Chelsea head coach following the 41-year-old's arrival earlier this week. Rosenior watched on from the stands at Craven Cottage on Wednesday evening to see his Blues side being beaten by Fulham in the Premier League.

The newly-appointed head coach will take charge of his first Chelsea game at the weekend with the Blues making the short trip to Charlton Athletic in the FA Cup third round. Calum McFarlane, who has taken charge of the last two matches as interim head coach, will become Rosenior's assistant at Stamford Bridge, football.london understands, after impressing during a tough period over the last week.


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