Hull vs. Middlesbrough Picks – Betting Preview, Team News, and EFL Play-Off Final Predictions (May 23) 

• When: Saturday, May 23, 2026. 10:30 AM ET
• Where: Wembley Stadium, London, England
• How to Watch: Paramount+

Match Result	Odds
Hull	+315
The Draw	+265
Middlesbrough	-120

Hull vs. Middlesbrough Preview

The richest game in club soccer is set for Wembley Stadium on May 23, as Hull City and Middlesbrough collide for a place in next season’s English Premier League. Much of the build-up for the season’s defining fixture has been dominated by off-field issues, with Southampton’s win in the semi-final overruled in court, handing Boro a second chance of promotion to the top-flight.

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Why are Middlesbrough in the EFL Play-Off Final?

Before going into our preview for the EFL Play-Off Final, it is worth examining why this season’s Wembley showpiece is so controversial. Southampton beat Middlesbrough in the semi-finals, but the backdrop for the tie was dominated by the Spygate Scandal before the first leg.

A Saints staff member was pictured taking videos at Middlesbrough’s training ground two days before the first leg, breaking EFL Rules. The hearing was heard on Tuesday, with Southampton also admitting to spying on Oxford United and Ipswich Town. The EFL decided to throw the Saints out of the playoffs, and implement a four-point deduction for the start of next season. Southampton appealed the decision, but they were unsuccessful.

The incident will continue to rumble on following the play-off final, with Wrexham and Millwall exploring legal challenges after missing out on the playoffs due to Southampton, while Hull City have also raised concerns, as they believe that Boro shouldn’t have been reinstated after losing their semi-final.

Hull Stats & Team News

Hull will have their sights set on a first Premier League return since 2016-17. The Tigers were excellent in their playoff semi-final second leg against Millwall, recording an excellent counter-attacking 2-0 win. Sergej Jakirović’s team stole the final playoff spot on the final day of the Championship season, beating Norwich City 2-1.

No side has been promoted to the Premier League via the playoffs after finishing sixth since Blackpool. Despite winning their semi-final, the Tigers have recorded just two wins in their last nine fixtures.

Likely Line-Up:

(3-4-2-1) Pandur (GK); Hughes, Egan, Ajayi; Coyle, Giles, Slater, Crooks; Belloumi, Millar; McBurnie

Middlesbrough Stats & Team News

After eight seasons in the Championship, Middlesbrough have been handed a second chance for promotion. However, it could be argued that this is effectively a third lifeline, as Boro had sat second for much of the regular season, before a loss of form saw them drop to fifth. A 2-1 defeat in their second leg against Southampton means that they have now failed to win in their last three, while Boro have recorded just two wins in their previous 12 fixtures.

Kim Hellberg has done an excellent job at the club since replacing Rob Edwards, while Morgan Whittaker and Tommy Conway have thrived at the top of the field. The strikers have scored 26 goals between them this term, and overall only Coventry, Ipswich, and Southampton scored more goals than Boro in the Championship.

Likely Line-Up:

(4-3-3) Dieng (GK); Ayling, Fry, Malanda, Targett; Brittain, Morris, Hackney; McGree, Whittaker, Conway

Head-to-Head Trends

• Middlesbrough have won three of their last five head-to-head encounters against Hull. However, the Tigers did win the latest meeting in December.
• Low-scoring affairs have been common between the sides, with two of the last three seeing under 2.5 goals scored. Three of the last four play-off finals have seen fewer than three goals scored.

Hull vs. Middlesbrough Picks

It’s hard not to feel sorry for Hull, as they are the innocent bystanders in the whole Spygate Scandal. But the fact that they were preparing for Southampton, before Boro’s reintroduction, means that they may not be prepared. Therefore, Boro are the standout chance to win at Wembley Stadium. However, the match on Saturday is unlikely to be the end of the drama.

• Middlesbrough @ -120 with BetOnline