Middlesbrough have put themselves in an excellent position to get promotion this season with a very strong squad but there will be some victims of that strong squad that surely seek a way out of the Riverside Stadium this winter, such as Leo Castledine.

Middlesbrough missed out on promotion by losing the play-off final to Hull City in May but Kim Hellberg was then given the funds to build what looks to be an extremely impressive squad this time around.

‘Boro spent heavily on the likes of Radek Vitek, Ashley Phillips, Max Arfsten and the current Championship top scorer Will Lankshear – among many others.

That has limited the minutes and importance of some of the other members of their squad, as a natural consequence, with Leo Castledine now struggling for game time after joining from Chelsea in January.

The former Shrewsbury Town and Huddersfield Town loanee has fallen down the pecking-order at the Riverside and was again an unused substitute for The Smoggies in their 2-2 draw against Cardiff City at the weekend.

As a result, it feels quite likely as though he may be loaned out again this winter and we have taken a look at four other players who will surely also depart Teesside in the January transfer window.

Alex Bangura

27-year-old Alex Bangura came through the academy at Feyenoord before beginning his professional career in the Netherlands at Cambuur ahead of a move to Middlesbrough in the summer of 2023.

After a stop-start debut campaign in terms of form, injury then prevented the versatile Sierra Leone international from making a single appearance in the 2024-25 campaign before becoming a bit-part player last season.

He was brought into the side on a semi-regular basis initially after the appointment of Hellberg last autumn but another injury in January limited his involvement for the rest of the campaign, albeit he did score in a 2-2 draw against Swansea City in April.

Bangura was left out of the squad for all three of their play-off matches in May, though, before being left out of the squad for the first half of the Championship season with his departure more or less now inevitable as a result of that omission.

George Edmundson

Having come through the academy at Oldham Athletic, George Edmundson became so highly-rated as a youngster that he was poached by Scottish giants Rangers in 2019.

Since moving to Ibrox, though, he has struggled for regular game time with a loan move to Derby County followed by a fairly lengthy stint as a periphery member of Ipswich Town’s rise from League One to the Premier League.

Eventually deemed surplus to requirements by The Tractor Boys as they returned to the top-flight, Edmundson spent the first half of the 2024-25 season on loan at Middlesbrough before moving on a permanent basis.

However, ever since becoming a permanently contracted player at ‘Boro, injuries and a loss of form saw Edmundson fall down the pecking-order with the likes of Alfie Jones, Adilson Malanda, Luke Ayling and Ashley Phillips ahead of him.

A departure to finally get back to playing more regularly would appear almost inevitable this winter as the 29-year-old seeks to reignite his career.

Law McCabe

Rather than someone who would surely be leaving ‘Boro on a permanent basis, such as Edmundson, young midfielder Law McCabe is a player that may well be searching for a loan move away this winter.

McCabe, born in Middlesbrough and a product of their academy, broke into the first-team picture at the Riverside at the back end of the 2023-24 campaign under the management of Michael Carrick, making three Championship appearances that season.

Mid-way through that season he signed a contract until the summer of 2027 and a need to showcase his abilities before potentially becoming a free agent at the end of this season is required for the 20-year-old.

McCabe spent some time out on loan in League One last season as he made 11 appearances for Plymouth Argyle as The Pilgrims struggled in the first half of the season before falling out of favour and returning to Middlesbrough mid-way through the campaign.

This season, McCabe has not yet made the bench for ‘Boro in the league, having been an unused substitute in their EFL Cup first round tie against Wrexham in August but he has captained their U21 side in Premier League 2 on three occasions and a departure this winter seems likely.

Micah Hamilton

Like Bangura, another player that has been left out of their squad in the Championship is former England youth international winger Micah Hamilton, whom Middlesbrough signed for around £2 million from Manchester City back in 2024.

Again, like Bangura, Hamilton was someone initially looked at by Hellberg with the young attacker starting on Boxing Day against Blackburn Rovers last season but that was his last appearance of the campaign and perhaps of his ‘Boro career.

Hamilton has struggled to live up to the promise that saw Middlesbrough shell out a hefty fee on him as a 20-year-old with a loan move to Stockport County in the second half of the 2024-25 campaign also an underwhelming one.

Left out of the squad this season, he may be a player that is either sold or loaned out with some League One clubs perhaps believing they can help him rediscover the promise that attracted Middlesbrough to him when he reached the fringes of the first-team picture at City.

Cruz Ibeh

Another youngster, like McCabe, who may be looking for a move away on a temporary basis as Middlesbrough focus themselves on promotion would be Cruz Ibeh.

The 18-year-old midfielder his highly-rated at the Riverside and he remains very young and raw, having celebrated his 18th birthday only earlier this month.

Having come through the ranks at ‘Boro, Ibeh made his debut for the club in an FA Cup third round defeat to Fulham before going on to play against Portsmouth in a 1-0 defeat in April and then, fairly remarkably, was brought on late on against Hull City in the play-off final at Wembley Stadium.

They remain his only appearances for the club but do suggest Hellberg is an admirer and so, unlike McCabe who may be coming to the end of his time on Teesside, Ibeh’s departure this winter would surely only be to aid his development and future progression further into the first-team at the Riverside.

David Strelec

Another big money signing from the past that has failed to hit the heights and may now be on his way out is Slovakia international striker David Strelec.

At his best, Strelec should bs someone who scores consistently at Championship level and becomes one of the better strikers in the division but his own inconsistency and a failure to seemingly fit into systems at Middlesbrough has undermined that.

The 25-year-old, who has 11 goals in 43 caps for his country and signed for Middlesbrough from Slovan Bratislava for around £6 million last summer, has scored eight goals in 34 Championship appearances for The Smoggies.

Mainly off the bench, that is not an atrocious return but the former Spezia forward has fallen down the pecking-order with the arrivals of Lankshear and Kyle Joseph, as well as Hellberg’s continued trust in and preference of Tommy Conway.

Having managed just two appearances this season with short cameos in draws against Burnley and Millwall, Strelec will surely be looking for a move away and, linked with a move to PAOK Salonika, may well be someone that Middlesbrough cash in on this winter.