This season, Middlesbrough has looked to the loan market to help fill the holes left by their approach to permanent transfers.
Two players, Sam Greenwood of Leeds United and Lewis O’Brien of Nottingham Forest, arrived in the summer. Two more players, Luke Thomas of Leicester City and Luke Ayling of Leeds United, joined the team in January. These players are the only ones from Daniel Farke’s Leeds team.
Here, we examine the players’ mixed fortunes and performances thus far this season, as well as the current state of affairs concerning the likelihood that Middlesbrough will pursue a long-term contract this summer.
Sam Greenwood
While Michael Carrick took his time to make sure the Leeds player understood exactly what was expected of him and how the team functions, Sam Greenwood settled into his Middlesbrough assignment. The 22-year-old appeared to be desperate to play and make an impression, and when given a run of games, he succeeded.
Riley McGree’s injury forced him to spend more time in the starting lineup, and he showed what he could do with six goals in eight games, including a magnificent free kick that won against Leicester.
Sadly, he has fallen further down the hierarchy and his goals and assists have somewhat stopped since. When he does don the Middlesbrough red shirt, there is no doubting his dedication. A player may become so driven to play and give it his all for the team that he occasionally commits needless fouls.
He still has eight games left in the season to make an impression.
What next?
Middlesbrough has wisely taken action to guarantee a set amount in the form of a buy option at the conclusion of the current campaign. If Michael Carrick and his group decide to pursue a long-term contract with the former Arsenal academy graduate, they will have to pay the agreed-upon sum of £1.5 million to acquire his services.
It is not quite that simple, as one might expect. Greenwood is probably going to demand a higher salary if Leeds were promoted because his current team would be in the Premier League. The player’s desire to join a team that is still in the Championship rather than staying at Leeds, which may be a top-tier team, is another minor issue.
Given a little slump in his play, Middlesbrough supporters may not be overly enthusiastic about the deal, but we must keep in mind that he is still only 22 years old and still developing. His technical skill set is excellent, and he might still be a good investment. No agreement
Lewis O’Brien
Carrick was well-versed in the Championship scene and knew what he was getting with Lewis. Although central midfield is unquestionably his best position, he was given enough confidence to start the season at left-back when injuries were common. Regretfully, O’Brien then sustained a serious injury that prevented him from playing from September to January: a fractured tibia and damage to his ankle ligaments.
His return to the team and his subsequent rise to prominence as one of the most reliable players is a credit to his character. He is regarded by Middlesbrough supporters as one of the best loan players in the group, if not the best, because of this.
What next?
O’Brien is on loan from Nottingham Forest, a team that may be demoted to the Championship after the current campaign. That might make it more difficult to determine whether the Midlands club still believes he has a future with them.
His Forest contract expires in2026, so they will still be able to play with him. The amount they could demand would largely depend on whether Middlesbrough pursues a deal or not. Even at 25, he still fits the dynamic of the recruitment model and would undoubtedly be a valuable addition to the team. Particularly considering that the talented Jonny Howson—who will turn 36 in May—won’t likely be around for the upcoming season.
He’s been playing some really good lately, winning man of the match against Leicester, among other things. He is an even better option because of his leadership abilities.
Carrick evaluated his comeback from injury by calling him a “special” character.
Carrick stated:
“He’s been excellent. He arrived on loan, started out as a left-back out of position, and then sustained an injury. He’s just now making his way back inside. But to be honest, he has a really unique personality and character around here.
There must be a deal on the horizon if Boro’s head coach can convince him to support their goals. Agree?
Luke Ayling
Ayling’s performances have been getting better over time. Till they switched to having three at the back, Middlesbrough let goals slip through their fingers like an old farm bucket. After making that small adjustment, Ayling performed better. With his legs tired from tracking the Championship’s devious, jet-heeled wingers, he was able to push up the pitch as a wing-back and support attacks, free from the constraints of his full-back duties.
Due to his reckless play style, he has managed three assists and is the ideal counterbalance for Lukas Engel, who also plays on the left side.
Ayling was selected more for his leadership qualities both on and off the pitch than for his skill on the pitch. His five yellow cards pretty much sum up his fighting abilities. He knows exactly how to manage games, even though you wouldn’t advise a player to accumulate too many cards. Something that Boro has previously struggled with.
What next?
It has been confirmed that Ayling will not be needed at Elland Road after his contract expires this summer. This season, he lost his starting spot to the unstoppable Archie Grey, and Leeds is obviously looking to change things up on the right side.
Thus, Ayling may very well be playing for his future at Middlesbrough this season, though he would have plenty of suitors in the event that Boro choose not to make a move for the seasoned, aggressive 32-year-old. This may be an exception, as Head of Football Kieran Scott and the recruiting staff typically favour acquiring players in the 18–24 age range. It might be wise for all sides to enter into a brief agreement. The future of Tommy Smith, another seasoned professional who is over 30, may also have an impact on Ayling’s decisions. Carrick might not have space for both of them, but he would welcome the assistance of an experienced player to help with the younger players in that position. Agree?
Luke Thomas
There’s no denying that Thomas hasn’t looked great when wearing a Middlesbrough shirt. With a strong background and 68 Premier League games under his belt, the Leicester left-back is not someone to be too hard on. He was brought in to help in Alex Bangura’s absence due to a chronic injury.
Regretfully, Carrick’s side experienced a mini-slump during his Boro games. Finding clean sheets was difficult, leaving the 22-year-old somewhat vulnerable. It should be noted that Middlesbrough’s attacking midfield is centred around whoever plays on the left side, be it McGree, Azaz, or Greenwood. They have a propensity to veer inside towards a ten. This occasionally exposes the left-back.
What next?
An intriguing one, given that his deal ends this summer. His career at Leicester seems to be in jeopardy, having already been loaned out to Middlesbrough and Sheffield United. A free transfer might make sense if Carrick is able to locate the player the team believed they would sign before the season ends. Priorities, however, were elsewhere because Bangura and Engel were more qualified to play left back or left wing back. Not a deal.
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