Middlesbrough have put themselves in a solid position to be promoted this season, but some of those players, such as Leo Castledine, will undoubtedly look for a route out of the Riverside Stadium this winter.

Middlesbrough missed out on promotion after losing the play-off final to Hull City in May, but Kim Hellberg was given the funds to put together what appears to be a very formidable group this time around.

Borough paid substantially on players such as Radek Vitek, Ashley Phillips, Max Arfsten, and current Championship leading scorer Will Lankshear, among others.

As a result, several of their other squad members’ minutes and importance have been reduced, with Leo Castledine struggling for playing time since coming from Chelsea in January.

The former Shrewsbury Town and Huddersfield Town loanee has dropped down the pecking order at the Riverside, and he was again an unused substitute in The Smoggies’ 2-2 draw with Cardiff City over the weekend.

As a result, it appears that he will be loaned out again this winter, and we have looked at four more players who will almost certainly leave Teesside during the January transfer window.

Alex Bangura

Alex Bangura, 27, graduated from Feyenoord’s youth before beginning his professional career in the Netherlands at Cambuur, with a move to Middlesbrough scheduled for the summer of 2023.

After a hit-or-miss rookie season, injury stopped the versatile Sierra Leone international from making a single appearance in the 2024-25 season, relegating him to a supporting role last season.

He was brought into the side on a semi-regular basis following Hellberg’s arrival last autumn, but another injury in January curtailed his involvement for the remainder of the season, though 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, but he was also left out of the team for the first half of the Championship season, making his departure all but inevitable as a result of that exclusion.

George Edmundson

George Edmundson came through the Oldham Athletic system and became so highly regarded as a teenager that he was signed by Scottish giants Rangers in 2019.

Since going to Ibrox, he has battled for consistent playing time, with a loan spell at Derby County followed by a lengthy period on the fringes of Ipswich Town’s journey from League One to the Premier League.

Edmundson was eventually deemed surplus to requirements by The Tractor Boys as they returned to the top division, therefore he spent the first part of the 2024-25 season on loan at Middlesbrough before making the permanent move.

However, after becoming a fully contracted player at Borough, injuries and a loss of form have caused Edmundson to fall down the pecking order, trailing Alfie Jones, Adilson Malanda, Luke Ayling, and Ashley Phillips.

As the 29-year-old attempts to restart his career, a departure to resume playing more regularly is nearly certain this winter.

Law McCabe

Rather than someone who would almost certainly leave Borough permanently, such as Edmundson, teenage midfielder Law McCabe could be looking for a loan transfer elsewhere this winter.

McCabe, a Middlesbrough academy product, burst into the first-team picture at the Riverside at the close of the 2023-24 season under Michael Carrick’s management, appearing in three Championship games that season.

Midway through the season, he signed a deal until the summer of 2027, and the 20-year-old will need to demonstrate his ability before potentially becoming a free agency at the end of the season.

McCabe spent some time on loan in League One last season, making 11 appearances for Plymouth Argyle as the Pilgrims battled in the first half before falling out of favour and returning to Middlesbrough midway through the season.

McCabe has yet to be on the bench for Borough in the league this season, having been an unused replacement in their EFL Cup first round fixture against Wrexham in August, but he has led their U21 team in Premier League 2 three times, and a move this winter is inevitable.

Micah Hamilton

Former England youth international winger Micah Hamilton, who Middlesbrough purchased for about £2 million from Manchester City in 2024, has also been left out of their Championship squad, similar to Bangura.

Hamilton, like Bangura, was first considered by Hellberg, with the youthful attacker making his debut on Boxing Day against Blackburn Rovers last season, but that was his final appearance of the season, and possibly his entire Borough career.

Hamilton has struggled to live up to the promise that prompted Middlesbrough to pay a high amount for him as a 20-year-old, and his loan move to Stockport County in the second part of the 2024-25 season has also been disappointing.

Left out of the squad this season, he may be sold or loaned out, with some League One clubs hoping to help him rediscover the promise that drew Middlesbrough to him when he was on the edges of City’s first-team picture.

Cruz Ibeh

Cruz Ibeh, like McCabe, could be seeking for a temporary move away while Middlesbrough focus on promotion.

The 18-year-old midfielder is highly regarded at the Riverside, and he is still extremely young and raw, having only turned 18 earlier this month.

After rising through the ranks at Borough, Ibeh made his FA Cup debut against Fulham in the third round, followed by a 1-0 loss to Portsmouth in April and, somewhat surprisingly, a late substitute appearance against Hull City in the play-off final at Wembley Stadium.

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

David Strelec

Slovakia international striker David Strelec is another big-money signing from the past who has failed to reach his full potential and may now be on his way out.

Strelec, at his best, should be a consistent Championship scorer who develops into one of the division’s finest strikers, but his own inconsistency and struggle to appear to fit into Middlesbrough’s systems has hampered that.

Middlesbrough’s leading scorers last season (all competitions)

PLAYER

POSITION

GAMES

GOALS

Morgan Whittaker: 41, 14; Tommy Conway: 47, 13; David Strelec: 31.

8

The 25-year-old, who has 11 goals in 43 matches for his country and joined Middlesbrough from Slovan Bratislava for about £6 million last summer, has eight goals in 34 Championship outings for the Smoggies.

That is not a bad return, but the former Spezia forward has dropped down the pecking order with the arrivals of Lankshear and Kyle Joseph, as well as Hellberg’s continued trust and preference for Tommy Conway.

Strelec, who has only made two appearances this season, with brief cameos in draws against Burnley and Millwall, will undoubtedly be eager for a transfer away and, having been linked with a move to PAOK Salonika, might be someone Middlesbrough try to sign this winter.