Middlesbrough are in for a busy winter season under Kim Hellberg. Having recently confirmed the signing of Chelsea offensive midfielder Leo Castledine, it appears that they will not be stopping there.

Swedish manager Kim Hellberg, who succeeded outgoing Rob Edwards in The Riverside dugout, seemed eager to impose his imprint on the Boro squad in January.

The Teessiders are in second position, just six points behind Coventry City, and appear to be a decent bet for promotion this season.

However, Hellberg has moved quickly this winter to strengthen his team and strive for promotion, having already completed the permanent signing of Chelsea starlet Leo Castledine.

Castledine shined for Huddersfield Town in League One throughout the first half of the season, scoring ten goals and assisting twice in 23 appearances, and now moves up to the Championship.

Boro don’t appear to be stopping there, with a bustling winter window set to shape them up for the remainder of the campaign, with Hellberg believing that the business done will propel them to the top flight.

Middlesbrough, Preston North End, and Blackburn Rovers have all scouted Davis Keillor-Dunn

Following Liverpool’s 4-1 FA Cup victory over League One Barnsley on Monday night, Pete O’Rourke stated that scouts from Middlesbrough, Preston North End, and Blackburn Rovers were dispatched to study Tykes forward Davis Keillor-Dunn ahead of a possible move.

According to the FLW exclusive, Barnsley are eager to split ways with the 28-year-old this winter in order to raise funds at Oakwell, which has sparked interest from teams in the division above.

Keillor-Dunn has 11 goals and one assist in 21 League One outings for Barnsley this season, despite the club’s troubles.

Middlesbrough are aiming to add depth and quality in the final third this January, even after signing Castledine, with the Barnsley forward surfacing as a possible alternative.

Middlesbrough likely to defeat Bristol City in the race for Aston Villa defender Finley Munroe.

Boro are seeking to improve in more areas than only forwards, having allegedly beaten Bristol City to the signing of Aston Villa defender Finley Munroe.

The Teesside club has negotiated a fee of around £300,000 for the left wing-back, who starred on loan with League Two Swindon Town in the first part of the season, scoring twice and assisting seven in 23 league games.

Swindon manager Ian Holloway has heaped praise on the 20-year-old, who seems ready to compete with Alex Bangura at left-back, saying: “I don’t think I’ve had a better full-back in my career. Maybe it’s Seamus Coleman. I believe Finn is in the same category.”

Munroe, who is still young and has plenty of time to grow, will move up two divisions to join Hellberg at The Riverside, bolstering the club’s left-back options as they aim for the Premier League.

Delano Burgzorg and Seny Dieng are likely to leave the club in January.

In terms of outgoings, it appears like forward Delano Burgzorg and goalkeeper Seny Dieng will be departing the club in January.

Burgzorg has piqued the interest of Bristol City, who are considered to be the frontrunners to sign the Surinamese.

The former Huddersfield Town player has made 22 league appearances for Boro this season, scoring once and assisting three times, but he is expected to be replaced by new signings this winter.

Dieng has been linked with a move to Hull City in January, with the EFL accepting the Senegalese shot-stopper’s free transfer, according to HullLive.

However, a stumbling block in the deal has emerged, with Dieng requesting a settlement from Boro to leave the club, according to Alan Nixon, with his £25,000-a-week earnings proving to be a difficulty that has yet to be resolved.

It remains to be seen whether Boro and Dieng can reach an agreement this winter, but the former QPR keeper, who hasn’t played a competitive game since December 2024, is plainly undesired on Teesside, and Boro are willing to reduce his pay in order to bring in new players.