Boro are looking to add to Kim Hellberg’s squad in the January transfer window
14:46, 08 Jan 2026
Leo Castledine of Huddersfield Town
Middlesbrough are close to signing attacking midfielder Leo Castledine after agreeing a fee with Chelsea.
The 20-year-old has starred this season on loan at Huddersfield, scoring 12 goals and adding five assists in 27 appearances. He’s been described by many as a ‘wonderkid’.
That form attracted interest from a number of Championship clubs, with Chelsea willing to use his form to sell him on this month, with just 18 months remaining on his Blues contract.
Though not yet recalled from his loan with the Terriers, a fee believed to be worth a little less than £1 million between Boro and Chelsea has been agreed, with the deal said to include a sell-on clause too. He will sign a long-term deal at the Riverside said to be for four-and-a-half-years.
Castledine will now travel to Teesside to negotiate terms with Boro before his Huddersfield loan is terminated and he makes the switch to Boro. He is set to become Boro’s first January signing.
It’s understood that Castledine’s arrival won’t end Boro’s pursuit of Brighton’s Jeremy Sarmiento. They’ve held talks with Brighton over a deal with the two-time promotion winner, but a deal has to make financial sense. They are said to have other forward targets too, as they look to strengthen Hellberg’s options.
Castledine will boost Boro’s forward options without needing to be registered in the EFL’s 25-man squad due to being under the age of 21. He is versatile and capable of playing anywhere across the forward line. He’s predominantly played as a ten for Huddersfield this season.
Incidentally, Castledine made his Chelsea debut against Boro, after coming through the academy with the Blues. He came off the bench in the second leg of the Carabao Cup semi-final in 2024, which Chelsea won 6-1.
He then made 27 appearances while on loan at Shrewsbury Town in League One last term, before really excelling this term at the Accu Stadium.
————
Here at TeessideLive, we are dedicated to bringing you the best Middlesbrough FC coverage and analysis.
Make sure you don’t miss out on the latest Boro news by joining our free WhatsApp group. You can get all the breaking news and best analysis sent straight to your phone by clicking here to subscribe.
Your information will be hidden, you’ll only ever receive messages from the Teesside Live sports team, and you can leave any time you like. To leave our community click on the name at the top of your screen and choose ‘Exit group’. If you’re curious, you can read our Privacy Notice.
You can also subscribe to our free newsletter service. Click here to be sent all the day’s biggest stories.
