Heartbreak for Boro after missing three chances to go up

May 23, 2026 No Comments

Heartbreak for Boro after missing three chances to go up Image source, Getty ImagesImage caption, Next season will be Middlesbrough’s 10th successive campaign in the ChampionshipByAdam LaniganBBC Sport England at WembleyPublished29 minutes agoOn an afternoon more suited to a day at the beach or jetting off to sunnier climes, Middlesbrough achieved unwanted history as their promotion dream died in agonising fashion at Wembley. After goalkeeper Sol Brynn could only palm away a cross, Oli McBurnie was on hand to score an injury-time winner that sent Hull City to the Premier League, and Boro’s third shot at promotion evaporated.Most teams only get two chances in one season to do it – either automatically or via the play-offs. Boro had an unexpected three and could not take any.It was not until the final day of the regular season that their hopes of a top-two finish were completely ended, before they were beaten over two legs by Southampton in the play-off semi-final amid the swirl of passion and ill-feeling over Spygate.Saints’ expulsion gave Boro a third and final chance to reach the Premier League, but again they could not take it.

So while the fallout of Spygate and the past fortnight will linger and rumble on, the real summer hurt will come, not from finding someone watching their training, but from not being able to capitalise on a glorious opportunity to end a nine-year exile from the top flight.

The month Boro might struggle to forget

2 May: Middlesbrough begin the day with an outside shot at automatic promotion. But they only draw at Wrexham and drop down a place to fifth, losing the chance to be at home in the second leg of the play-offs.

The draw also allows Hull to leapfrog the Welsh club and claim the final spot in the play-offs.

7 May: Southampton intern Will Salt is found at Boro’s Rockliffe Park training ground attempting to record a training session, contravening English Football League regulations.

9 May: Boro host Saints in the first leg of the play-off semi-final at a fired-up Riverside Stadium.

Despite bombarding the visitors’ goal, especially in the first half, they fail to score and the game ends goalless.

12 May: The return leg at St Mary’s is another full of drama as, despite scoring early, the Teessiders cannot hang on and are beaten deep into extra time to send Southampton into the final. Or so it seemed.

19 May: An Independent Disciplinary Panel rules Southampton guilty in the Spygate scandal and they are kicked out of the play-off final, with Middlesbrough reinstated.

20 May: Southampton appeal against that decision, but the sanction is upheld by a separate panel and Boro’s place at Wembley is rubber-stamped.

23 May: Middlesbrough lose the play-off final to Hull after an injury-time winner.

Hull promoted with late Wembley winner against Boro
Southampton expelled from play-offs for spying
Charles sends Saints past Boro and into play-off final
Southampton face EFL probe over alleged spying on Middlesbrough

Kim Hellberg looking down at the floor, while scratching his face with his right hand at Wembley — Image caption,

Kim Hellberg has won 14 of his 33 games in charge of Middlesbrough

Hellberg ’empty’ after Boro heartbreak

Head coach Kim Hellberg called this period a “rollercoaster of emotions” as despite doing so many things going well during the season, Boro were left with nothing tangible to show for it.

They spent 35 of the 46 matchdays in the Championship’s top two and went top in early February after a sparkling spree of six straight wins, but they were crucially undone by a late run of only two wins in 10 games.

The Swede has been a revelation since he replaced Rob Edwards in November after his predecessor’s departure for Wolves, with his team playing some great football and the 38-year-old’s humility really shining through with the Teesside public.

But Hellberg’s biggest task possibly lies ahead of him in the coming weeks in picking up the whole club to go again come August.

“It’s been two heart-breaking losses in two weeks, which makes it very, very tough,” he mentioned.

“It’s been an emotional drain, so when the game ended today, you feel very, very empty. Disappointed, sad, flat in emotional terms.

“All the things you put into the year and into training sessions. It’s a very tough moment, a sad moment.

“I wish I could have done better through this period – that’s what I always go to. I wish I could have found better solutions when we didn’t score those goals.

“It’s my responsibility and I have to try after the break to develop myself to help the players better to score more and create more and work forward.”

Wembley misery continues

More than 35,000 Middlesbrough fans made it to Wembley with little more than 48 hours’ notice, taking over Trafalgar Square on Friday night and turning the capital red.

The club and the town has been united in anger over the events of Spygate and they were hoping to use that as fuel to deliver the longed-for promotion.

But despite this unexpected second crack at the play-offs, they could not shift something else that hangs over the club – their wretched Wembley record.

That now stands at played six, drawn one, lost five, across 36 years, taking in cup finals and play-off finals.

Two of those visits came in the 1996-97 season when they lost both the FA Cup final and the League Cup final (in a Hillsborough replay to Leicester City after drawing the first game).

That campaign draws parallels to this one as it also included the triple whammy of relegation from the Premier League on the final day despite containing a side with the likes of Juninho and Fabrizio Ravanelli.

There was also off-field drama for Bryan Robson’s team, with a points deduction for failing to fulfil a league fixture at Blackburn Rovers because of illness in the squad, with those three points costing them survival.

Nearly three decades on, the mix of emotions from that season remains, and it will be the same from 2026 – one that has provided so many great moments but has been dwarfed by crushing disappointment.

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