Middlesbrough & Hull City involved in eleventh hour transfer twist | OneFootball

Kyle Joseph's situation at the MKM Stadium has been in the spotlight across recent days

Middlesbrough will be hoping the 2026/27 season is the one in which they are finally able to end their lengthy exile from the Premier League, having come agonisingly close to achieving promotion on two counts in a dramatic 2025/26 campaign at the Riverside Stadium.

Indeed, the upcoming Championship term will also be the first full season Boro have under Kim Hellberg, who was drafted in as Rob Edwards' replacement on Teesside after the 43-year-old initially joined Wolves in controversial circumstances.

Despite being in the promotion conversation for large portions of the season, Middlesbrough were not able to see their performance levels in last season's final weeks be reflected in the scoreline, as they fell out of the automatic promotion places and failed to win the play-offs afterward.

The spygate scandal, which is still ongoing to an extent, between themselves and Southampton eventually saw Hellberg's side reinstated into the post-season lottery, but their winless record at Wembley Stadium continued when Oli McBurnie's 95th-minute goal promoted Hull City back to the top-flight at the Reds' expense.

As a result, Middlesbrough will look to make their mark once again in what is set to be an even more compelling promotion picture in 2026/27 due to the expansion of the play-off format.

Ironically, Hellberg's team have recently been linked with a move for Hull forward, Kyle Joseph, who wasn't involved in the play-off final, and now it appears as though he may not be bound for the North East after all.

Eleventh-hour transfer twist involving Kyle Joseph emerges between Middlesbrough and Hull City

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Joseph's first full season at the MKM Stadium ended in circumstances which no one saw coming for Sergej Jakirovic and his squad, with the forward initially being recruited by the Tigers from League One side, Blackpool, for a reported £2.5m in January 2025 after initial interest was exclusively revealed by Football League World.

The attacker initially struggled to make an impact in his first months in East Yorkshire, before eventually breaking his duck on the goalscoring front with a consolation in a 4-2 defeat to Bristol City at Ashton Gate 11 months ago.

Despite previously being deployed as a central striker by Selles, Jakirovic, at times, has opted to use the 24-year-old on the right flank, making his versatility and work-rate a real asset in the club's eventual play-off success.

Yet, after scoring eight times, he was ruled out of the play-off final due to an ankle injury sustained in the second leg of the semi-final against Millwall, which was expected to keep him sidelined for a 10-week period.

It was then claimed that the Lions would make a £5m bid of their own, before links with Middlesbrough for the same value surfaced as it became abundantly clear that City needed to generate approximately £6m to avoid a punishment due to an overspend in relation to the EFL's accounting regulations.

However, the sales of Ivor Pandur and Aidon Shehu to Rangers and Panathinaikos respectively have wiped out those concerns, while Joseph's move was said to be hanging in the balance earlier in the week, even though the initial £5m sum had been agreed between the two clubs.

It has now been reported by Pete O'Rourke of Football Insider that the move for the London-born forward is OFF completely due to a breakdown in negotiations, meaning Middlesbrough are likely to turn their attention to other options, while Joseph's own future at the MKM remains uncertain.

Middlesbrough closing in on £0 transfer after Kyle Joseph blow

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It would have been interesting to see whether Joseph would have been utilised as a main striker option given David Strelec and Kaly Sene's struggles in their first seasons at the Riverside while Tommy Conway remains on the sidelines himself, or whether the forward would have competed with the likes of Morgan Whittaker to start in the wide areas.

However, such news comes as a blow just hours after Hayden Hackney's expected exit to Everton in a £24m deal was confirmed, but it appears that Middlesbrough are wasting no time when it comes to adding reinforcements.

According to the Northern Echo, Hellberg is closing in on a deal to sign free agent, and fellow versatile winger/attacking midfielder, Myles Peart-Harris, who recently left Brentford after a loan spell with Oxford United last term.

Such developments will see them edge out Queens Park Rangers and Leicester City, whose initial interest in the 23-year-old was exclusively broken by FLW.