Why Middlesbrough will feel major Hull City transfer regret after Wembley | OneFootball

The Reds passed up a chance to sign one of City's promotion heroes earlier this season

The somewhat strange nature of football has certainly been on show in this season's Championship, and Middlesbrough will know about that feeling more than most clubs.

It has now been 11 years since the Teesside outfit won promotion to the Premier League under Aitor Karanka, with not many giving them a chance of achieving such feats before the campaign got underway in August, initially under Rob Edwards.

Of course, his spell at the Riverside Stadium set the wheels in motion for a potential promotion push before a controversial exit to Wolves, who will be making their first visit to Teesside in eight years next season after being relegated from the top-flight.

Kim Hellberg was then able to largely continue building upon such momentum throughout his opening months as head coach, before a rocky spell from March onwards saw Boro's promotion credentials come under intense scrutiny.

However, they were still not questioned as much as Hull City's, even though Sergej Jakirovic had the Tigers positioned inside the Championship's top six for 24 consecutive matchdays between January and April, before climbing back into sixth on the final day ahead of a dramatic play-off campaign.

Boro, of course, were reinstated to play City at Wembley Stadium in the play-off final after the spygate fallout, and then were on the wrong end of further drama through Oli McBurnie's 95th-minute strike after Sol Brynn failed to gather Yu Hirakawa's fizzing cross.

Some believe that Hull's promotion was a rightful sense of footballing 'justice', but for those in the North East, it served another regretful reminder aside from letting top-flight football slip away from their grasp.

Middlesbrough showcased previous transfer interest in Hull City ace Charlie Hughes

As well as seeing three former players in Paddy McNair, Ryan Giles and Matt Crooks achieve play-off success with the Tigers - some three years after they were involved in Boro's semi-final loss to Coventry City - it would have also been a painful watch for those on Teesside to see Charlie Hughes on the winning side at their expense.

The 22-year-old has been one of the most highly-rated homegrown talents in the EFL for some time, with Hull's £3.5m acquisition of his services from Wigan Athletic two summers ago now proving to look a bargain.

Indeed, after excelling in his first season in HU3 despite the fact Hull only staved off relegation to League One on goal difference, the England youth international was linked with the likes of Sheffield United and the Sky Blues - with the latter seeing three bids, rising as high as £12m, rejected by Acun Ilicali.

After continuing his upward trajectory in the opening half of Jakirovic's first season as head coach, Football League World exclusively broke the news that Boro were eyeing up an ambitious move for the centre-back, that would have also set Steve Gibson back over £10m.

Ultimately, a move came to no avail, and with Reds supporters recently bemoaning a lack of ambition throughout the winter window, Hughes was a colossal figure for the East Yorkshire outfit as they went on to punish a lack of cutting edge from the likes of Morgan Whittaker and David Strelec, in particular, in North London.

That is despite that, until McBurnie's winner, Boro's own back-three of Luke Ayling, Dael Fry and Adilson Malanda, all performed to a relatively solid degree.

Sergej Jakirovic's verdict on Hull City's Charlie Hughes has come to fruition

During his Wigan days, Hughes was linked with moves to Brentford and West Ham - then of the Premier League - before making the initial step-up to the Championship with Hull under former boss, Tim Walter.

Even during a difficult debut - a 4-0 loss to Norwich City in October 2024 - there were signs of promise, and after the aforementioned links to Coventry and the Blades last summer, Jakirovic was certainly more than confident that his prized asset would be a top-flight performer sooner rather than later.

"So (in) my opinion, anything below his value we don’t need to speak at all. I will not even pick up the phone because he’s very good, and for me, his next move is to the Premier League, not the Championship," the Bosnian said back in August.

Those words have now been vindicated, and it has emerged that Hughes is potentially in line for a contract extension ahead of the first top-flight campaign of his career, whilst Middlesbrough and Hellberg are left to take their medicine and conduct a squad reshuffle in the hope of following in City's footsteps in 12 months' time.