Everything you need to know as Middlesbrough sign Leo Castledine from Chelsea
17:17, 09 Jan 2026
Middlesbrough sign Leo Castledine from Chelsea
Middlesbrough sign Leo Castledine from Chelsea(Image: )
Middlesbrough have confirmed the signing of Leo Castledine from Chelsea on a long-term deal.
The versatile forward spent the first half of the season on loan at Huddersfield Town, where his form attracted the attention of a number of Championship clubs. But Boro have won the race for his signature.
The 20-year-old has signed a four-and-a-half-year deal at the Riverside. Boro will initially pay a little under £1 million for Castledine’s signature, with the deal also including a future sell-on fee for Chelsea.
Castledine will go straight into Boro’s first-team picture to boost Kim Hellberg’s attacking options. But crucially, he is under-21 and therefore does not have to be included in the EFL’s 25-man-max registration list.
On joining Boro, he said: "I’m absolutely over the moon to join what is a massive, massive club. 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."
Speaking earlier in the day, Hellberg said: "He’s a good player. He’s done a brilliant job at Huddersfield - doing a lot of good stuff. He is capable of scoring a lot of goals. So he is a good player.”
Boro were one of many interested in Castledine this month, with Chelsea keen to capitalise on his form with Huddersfield this season and cash-in with only 18 months left on his contract.
At the Accu Stadium, Castledine has managed 12 goals and five assists in 27 appearances. He also made 27 appearances for Shrewsbury Town last season, and actually made his professional debut for Chelsea against Boro in the second leg of the Carabao Cup semi final in January 2024.
Described previously as a ‘wonderkid’, Castledine impressed Chelsea legends Frank Lampard, Ashley Cole and John Terry when in the Blues’ academy. He has also been capped by England from under-15 to under-19 level thus far.
A versatile player, he’s predominantly operated as a number ten for Huddersfield this season, scoring some highlight-reel goals. But he can also play as a wide forward or further back in the centre of midfield.
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