Middlesbrough missed a third chance to reach the Premier League after losing the play-off final to Hull City in injury time.
On a day better suited for beach trips or overseas getaways, Middlesbrough faced a crushing setback at Wembley as their promotion ambitions were shattered in dramatic fashion. With goalkeeper Sol Brynn unable to hold a cross, Oli McBurnie pounced in stoppage time to score the winner, eliminating Boro's third promotion opportunity of the season. Most teams only get two cracks at promotion either automatically or through the playoffs, but Middlesbrough found themselves with an unexpected third attempt and squandered it completely.
Their hopes of securing a top-two finish vanished on the final day of the regular season before they were knocked out of the playoffs by Southampton in a controversial two-legged semi-final amid the controversy surrounding Spygate. The Saints' expulsion from the final handed Middlesbrough their long-awaited third chance to reach the top flight, but once again they failed to capitalize. While the fallout from Spygate and the recent events will continue to simmer, the true summer agony will stem not from external spying but from failing to seize a golden chance to end a nine-year absence from England's elite division.
7 May: Southampton's Will Salt was discovered at Middlesbrough's Rockliffe Park training ground attempting to record a session, breaching English Football League rules.
9 May: Boro faced Southampton in the first leg of the playoff semi-final at a charged Riverside Stadium. Despite dominating possession, especially in the opening half, they failed to find the net and the match finished goalless.
12 May: The return fixture at St Mary's turned into a thriller as Middlesbrough took an early lead but were pegged back and eventually beaten in extra time, sending Southampton to the final — or so it appeared.
19 May: An Independent Disciplinary Panel found Southampton guilty in the Spygate scandal and expelled them from the playoff final, reinstating Middlesbrough.
20 May: Southampton lodged an appeal against the ruling, but the sanction was upheld by another panel, confirming Middlesbrough's place at Wembley.
23 May: Middlesbrough lost the playoff final to Hull City after a dramatic injury-time winner ended their promotion dream.
Head coach Kim Hellberg described the season as a 'rollercoaster of emotions' after his side produced strong performances yet finished with nothing to show for it. Middlesbrough spent 35 of 46 matchdays in the Championship's top two and topped the table in early February following an impressive run of six consecutive wins, but a late dip—just two victories in their last 10 games—proved their undoing. Since taking charge in November following Rob Edwards' departure to Wolves, Hellberg has impressed with attractive football and a humble approach that resonated with the Teesside faithful. Now, his biggest challenge lies in rallying the entire club to regroup and mount another promotion push come August.
'It's been two heart-breaking losses in two weeks, which makes it very, very tough,' he said. '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.'
Over 35,000 Middlesbrough supporters traveled to Wembley with under 48 hours' notice, occupying Trafalgar Square the previous night and painting the capital red. The club and local community united in anger over the Spygate controversy and hoped to channel that energy into securing long-awaited promotion. Yet despite this unexpected reprieve in the playoffs, they were unable to overcome another persistent burden — their dismal Wembley record. Across 36 years, they have played six times at the national stadium, drawn one, and lost five, including cup finals and playoff finals. Two such visits came in the 1996–97 season when they lost both the FA Cup and League Cup finals, the latter replayed at Hillsborough after a draw against Leicester City. That campaign echoes this one, featuring a trio of setbacks: relegation from the Premier League on the final day despite a squad boasting talents like Juninho and Fabrizio Ravanelli, and an off-field crisis with a points deduction for failing to fulfill a fixture at Blackburn Rovers due to illness, costing them three points and survival. Nearly three decades later, the mixture of emotions from that season lingers, and the same sentiment will define 2026 — a year filled with memorable moments yet overshadowed by crushing disappointment.