The YP FootballTalk Podcast: Yorkshire's Christmas and New Year winners and losers
Fulham v Middlesbrough NEW Middlesbrough signing Leo Castledine has pledged to hit the ground running after completing his permanent move to the Teessiders - becoming the first signing of the Kim Hellberg era in the process.
The attacking midfielder, who had a stellar loan spell in the first half of 2025-26 at Huddersfield Town, has signed a four-and-a-half year deal with Boro, who won the race for the services of the 20-year-old Chelsea star, who had been interesting a number of Championship clubs.
Castledine excelled in his time at Town, scoring 12 times in 27 appearances before being recalled early from his season-long loan in West Yorkshire by the Stamford Bridge club.
The 20-year-old, who spent time on loan at Shrewsbury Town last term, 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.
Leo Castledine, pictured during his loan spell at Huddersfield Town. He has now completed a full-time move from Chelsea to Middlesbrough.placeholder image
Leo Castledine, pictured during his loan spell at Huddersfield Town. He has now completed a full-time move from Chelsea to Middlesbrough.
"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."
Castledine hails from Kingston-upon-Thames and his new club call in not too far away for a third-round cup tie where they will be backed by a sell-out contingent of almost 5,000 fans in the Putney End.
A similarly big following witnessed a thriller which had significant and fateful connotations in Boro's quest to finish in the Championship's top two in 2014-15 when the Teessiders lost 4-3 in April 2015.
Middlesbrough manager Kim Hellberg. Picture: Nigel French/PA Wire.placeholder image
Middlesbrough manager Kim Hellberg. Picture: Nigel French/PA Wire.
On this occasion, the pressure will be off somewhat against their top-flight hosts, whose numbers including ex-Boro loan striker Rodrigo Muniz.
Boro boss Hellberg said: "The players are looking forward to challenging themselves and seeing how good we can play against a very good Premier League team away from home.
"There’s such a big interest in English football in Sweden. I always watched these (Cup) games at home because I’ve been following English football for over 30 years. It will be great to take part in this cup and will be a special moment in a lot of ways."