Hull City and Middlesbrough meet on Saturday evening, 23 May 2026, with a place in the Premier League on the line. After a grueling Championship campaign, this play-off final represents the ultimate test of nerve.
The build-up to this fixture has been anything but ordinary. Hull booked their place in the final with a clinical 2-0 aggregate victory over Millwall. Middlesbrough, meanwhile, find themselves in the final after a dramatic off-field turn of events. Despite drawing 1-1 with Southampton in their second leg, Boro were reinstated to the final following Southampton's expulsion from the play-offs over a spygate scandal. With the off-field drama now settled, both managers must focus entirely on ninety minutes of high-stakes football.
Hull City Form & Analysis
Hull City manager Sergej Jakirović described reaching this final as the biggest achievement of his career. His side showed immense patience and defensive discipline to get past Millwall in the semi-finals, drawing 0-0 at home before producing a clinical 2-0 victory at The Den. Goals from Mohamed Belloumi and Joe Gelhardt secured that crucial second-leg win, showing that the Tigers have the quality to hurt teams on the break.
However, Jakirović has several selection headaches ahead of the trip to Wembley. Midfielder Eliot Matazo is out with a serious knee injury, and forward Kyle Joseph is sidelined with an ankle problem. There are also late fitness tests required for Cody Drameh, Toby Collyer, and Amir Hadziahmetovic.
Hull have won two, drawn three, and lost one of their last six matches. While they are currently on a three-game unbeaten run, their squad depth will be tested to the limit if those doubtful players fail to recover in time.
Middlesbrough Form & Analysis
Middlesbrough head coach Kim Hellberg will feel his side has been handed a second lifetime after the extraordinary events of the past week. Boro are currently on a six-game unbeaten run, though their last three matches have ended in draws, including the 1-1 result against Southampton where Riley McGree opened the scoring early on.
In terms of team news, Middlesbrough will have to cope without forward Tommy Conway, who is ruled out with an ankle injury. On a more positive note, Hellberg has confirmed that key midfielder Hayden Hackney is back in contention after recovering from a groin layoff. Having Hackney back in the engine room provides a massive boost to Boro's transition play.
Middlesbrough have shown plenty of attacking intent recently, highlighted by a 5-1 thrashing of Watford late in the regular season. They will look to impose their tempo early on and exploit any defensive gaps left by a depleted Hull side.
## Head-to-Head
Recent meetings between these two sides suggest we should expect goals. In their last encounter in December 2025, Hull managed a narrow 1-1 away win at Middlesbrough. However, just a few weeks earlier in the same month, Middlesbrough ran riot at Hull, securing a dominant 4-1 victory.
Over the last few seasons, Middlesbrough have generally had the upper hand, including a 3-1 home win in late 2024 and a 1-0 victory at Hull earlier that same year.
We Predict: Away Win
Middlesbrough enter this final with the psychological lift of their reinstatement and the crucial return of Hayden Hackney to the midfield. While Hull City showed great defensive resilience against Millwall, their growing injury list could prove to be their undoing under the Wembley arch.
With key players missing or doubtful for the Tigers, Middlesbrough look well-placed to capitalise. Hellberg's side has the attacking quality to break down Hull's backline, especially with McGree in good form.
We are backing an Away Win for Middlesbrough in normal time at 1.7963, with a 1-2 scoreline looking like a very plausible outcome.
