Middlesbrough will be hopeful that the 2026/27 season will mark the end of their long absence from the Premier League, after coming agonisingly close to promotion on two occasions during a dramatic 2025/26 campaign at the Riverside Stadium.

Indeed, the 2017 Championship season will be Boro’s first complete season under Kim Hellberg, who was brought in to replace Rob Edwards on Teesside after the 43-year-old moved Wolves in contentious circumstances.

Despite being in the promotion debate for much of the season, Middlesbrough’s performance in the final weeks of last season did not reflect in the scoreline, as they dropped out of the automatic promotion places and failed to win the play-offs.

The spygate scandal, which is still ongoing to some extent, between them and Southampton eventually saw Hellberg’s side reinstated in the post-season lottery, but their winless record at Wembley Stadium was extended when Oli McBurnie’s 95th-minute goal propelled Hull City back to the top flight at the expense of the Reds.

As a result, Middlesbrough will attempt to make their imprint once more in what promises to be an even more interesting promotion picture in 2026/27, thanks to the extension of the play-off system.

Ironically, Hellberg’s team has lately been connected with a move for Hull forward Kyle Joseph, who was not part in the play-off final, but it now appears that he may not be heading to the North East after all.

An eleventh-hour deal twist involving Kyle Joseph arises between Middlesbrough and Hull City

Joseph’s first full season at the MKM Stadium ended in unexpected circumstances for Sergej Jakirovic and his squad, with the forward joining the Tigers from League One side Blackpool for a reported £2.5 million in January 2025, as exclusively revealed by Football League World.

The forward struggled to make an impact in his first months in East Yorkshire until breaking his goal-scoring drought with a consolation in a 4-2 defeat to Bristol City at Ashton Gate 11 months ago.

Despite previously being employed as a central striker by Selles, Jakirovic has occasionally preferred to utilise the 24-year-old on the right side, making his adaptability and hard ethic a valuable asset in the club’s eventual play-off victory.

However, after scoring eight goals, he was ruled out of the play-off final due to an ankle injury received in the second leg of the semi-final against Millwall, which was projected to keep him out for ten weeks.

It was then suggested that the Lions would make their own £5 million bid, before ties with Middlesbrough for the same price appeared when it became evident that City needed to generate around £6 million to avoid a fine for overspending in accordance with the EFL’s accounting rules.

However, the sales of Ivor Pandur and Aidon Shehu to Rangers and Panathinaikos, respectively, have alleviated those fears, while Joseph’s transfer was thought to be in doubt earlier in the week, despite the fact that the initial £5 million fee had been agreed upon between the two clubs.

According to Pete O’Rourke of Football Insider, the transfer for the London-born attacker is now officially off due to a breakdown in negotiations, which means Middlesbrough will likely look into other possibilities, while Joseph’s own future at the MKM remains uncertain.

Middlesbrough are closing in on a £0 move after Kyle Joseph blow.

It would have been interesting to see if Joseph would have been used as a primary striker option given David Strelec and Kaly Sene’s struggles in their first seasons at the Riverside, while Tommy Conway remains sidelined, or if the forward would have competed with Morgan Whittaker for a starting spot in the wide areas.

However, such news comes just hours after Hayden Hackney’s likely £24 million transfer to Everton was revealed, although Middlesbrough appears to be moving quickly to recruit reinforcements.

According to the Northern Echo, Hellberg is close to signing free agent Myles Peart-Harris, a versatile winger/attacking midfielder who recently left Brentford following a loan spell with Oxford United last season.

Such events will put them ahead of Queens Park Rangers and Leicester City, both of whom had expressed an interest in the 23-year-old before FLW announced the news.

However, with plenty of time remaining in the transfer window, Middlesbrough will undoubtedly continue to make additions.