Middlesbrough eyeing up Huddersfield Town transfer swoop | OneFootball

Boro are looking to raid the Terriers for one of their young talents this summer

Middlesbrough may have important sights set on the upcoming Championship play-off semi-finals against Southampton, but they will have to also keep tabs on any potential transfer business.

There has already been chaos on the eve of the visit of the Saints this coming weekend, with the Teessiders reporting their opponents to the EFL after an alleged case of spying by a member of staff at their Rockliffe training base - much like what happened with Leeds United and Derby County back in 2019.

It's added a bit of unexpected spice to the encounter, and whilst on the pitch Boro will be hoping to navigate their way to Wembley, the work has not stopped off the pitch - particularly when it comes to new recruits for the club's under-21's side.

Boro have a category one academy system, with their under-21's playing in the Premier League 2 competition along with most of the top flight of English football, and they are always actively looking for new recruits to potentially develop and one day head to the first-team.

And they are now looking towards League One outfit Huddersfield Town in a bid to perhaps add another promising youngster to their ranks ahead of the 2026-27 season.

Middlesbrough plotting Huddersfield Town transfer raid

According to a report from Football Insider, Boro are exploring a move for Terriers starlet Jay Smith-Sway as a development project.

The 19-year-old is said to have one year remaining on his current contract at the Accu Stadium, and has not been offered fresh terms as it stands by the West Yorkshire outfit.

A right-back who can also play in midfield, Smith-Sway started off at Everton's academy before joining Town in 2023, and is yet to make a league appearance for Huddersfield, although he did make his senior debut back in August 2025 when coming off the bench in an EFL Cup clash with Leicester City.

The teenager made six appearances across that competition and the EFL Trophy in 2025-26, but also spent time out on loan at Hartlepool United of the National League, where he played five times under Nicky Featherstone at the back end of their campaign.

Per Football Insider's report, Boro would look to immediately loan full-back/midfielder Smith-Sway out to aid his development if they were able to agree a deal with Huddersfield for his services, rather than placing him in the under-21's squad to play against other reserve sides.

Jay Smith-Sway would fit in with recent Middlesbrough recruitment trend

Boro's recruitment isn't all about their first-team - they've been very active in recent years in trying to bolster their under-21's side to be competitive in the Premier League 2 competition.

When you look at this past season, Boro took goalkeeper Owen Foster from Hull City and Spurs defender Archie Baptiste from their respective development squads, whilst also keeping an eye on local non-league talents, as well as the lower reaches of the pyramid further afield, as evidenced by bringing in Oxford City's Jayden Carbon.

In-fact, Boro looking at Huddersfield's youth prospects isn't a new thing either, given they signed Hazeem Bakre from the Terriers in the 2024-25 season, although after a prolific first season with seven goals in 11 under-21's league matches for the Teessiders, the forward had a bit of a stop-start 2025-26.

If Boro's recruitment team sees something in Smith-Sway and his potential, then on recent evidence, they're likely to land him - if that does happen though, expect the teen to be out on loan pretty quickly to get up to speed with more men's football.