The 3 Middlesbrough players set to leave as a free agent this summer | OneFootball

Boro look set to make some tough decisions over the futures of some much-loved and important out of contract players.

Middlesbrough are set to face a number of tough contract decisions ahead of the 2025/26 season.

Boro will be hoping to make those calls with Premier League preparations in mind, as Michael Carrick looks to mastermind a big promotion push in the final months of the season.

The Teessiders have found themselves stuck in the Championship since their relegation from the Premier League in 2017, with multiple play-off heartbreaks and the odd brush with relegation in the years since.

With Carrick's squad laden with quality players and big-money profits being made on numerous stars in recent times, the future does appear to be bright at the Riverside Stadium. But, who may not be around to continue on the club's journey in the coming years?

Football League World takes a look at the three Middlesbrough players who are set to leave the club as free agents at the end of the season.

Anfernee Dijksteel

One of Middlesbrough's surprise success stories of the 2024/25 season has been the resurgence of right-back Anfernee Dijksteel.

The 28-year-old had been out in the Teesside over the last two seasons, having made just 23 and 22 appearances in all competitions in the previous two campaigns.

He'd been one of the first names on the teamsheet at the Riverside during his first few years with the club following his move from Charlton Athletic in 2019, but a combination of injury setbacks and others being preferred ahead of him have limited his game time significantly in recent times.

As such, entering the final year of his Boro contract, it appeared to be a foregone conclusion that he would be sold in the summer, but no transfer ever materialised. Luckily for Middlesbrough too, as the Suriname international has been enjoying some of his best football in a red and white shirt this season.

Bagging his first couple of goals for the club as well as showcasing his ability to be a really solid player at second tier level, Dijksteel has played a vital role in Carrick's side so far this term, despite injury woes once again capping his impact.

Late interest from a number of Championship clubs arrived for him during the winter window, but with no time to source his replacement, Middlesbrough decided to keep him around. But with the future of their right-back spot far from certain, Boro could do far worse than handing him a new contract before he hits the free agent market.

Tommy Smith

A player who Middlesbrough have perhaps been missing more than they realise this season, Tommy Smith hasn't kicked a ball for Boro since rupturing his Achilles in October 2023.

The 32-year-old right-back had been Carrick's first-choice option on the right side of his defence during the 2022/23 season, in which the former Stoke City and Huddersfield Town man made 40 appearances in all competitions.

Out of contract in the summer, should he be unable to retake the field this season, the veteran full-back won't have the chance to prove his fitness and importance to the squad, and that could cost him dearly.

However, with Boro's long-term right-back situation being unclear as mentioned previously, the club's hierarchy may see it wise to hand Smith a short-term extension.

Jonny Howson

Middlesbrough's captains armband has been worn by some true leaders and widely adored figures in recent times, and Jonny Howson is one of them.

However, the time for him to pass it on to the next Boro skipper may well be nearing, as the 36-year-old central midfielder is out of contract at the end of the season.

One of the features of his reign as Boro's captain over the years has been his reliability and dependency, having barely missed a game for the club since signing from Norwich City in 2017.

In fact, the fewest number of matches he's played in all competitions during his Middlesbrough career so far is 43, highlighting just how much of a stalwart he's been in Boro's engine room.

But, injuries have arrived for the evergreen midfielder this term, and that has seen him take a step backwards into more of a squad role, allowing Hayden Hackney and Aidan Morris to form a midfield partnership to perhaps take the club into the future.

If 2024/25 is to be his final season at the Riverside Stadium, he will leave as one of the most well-loved Boro players of his time, and a truly great servant to Middlesbrough Football Club.