Anthony Elanga blazed the decisive spot-kick over the bar as Middlesbrough knocked Man Utd out of the FA Cup via a penalty shootout.
Paul Pogba made his first appearance in three months for the Red Devils.
The 28-year-old returned from a thigh injury in Friday’s encounter at Old Trafford, where goalkeeper Dean Henderson made his third start of the season.
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Hannibal Mejbri, 19, was named among the substitutes against a Middlesbrough side including former United player Paddy McNair.
United hit the crossbar inside 80 seconds.
Goalkeeper Joe Lumley failed to deal with a long ball forwards from Luke Shaw and Jadon Sancho reacted with a superb clipped effort that hit the bar. Bruno Fernandes could not turn home the rebound.
United wasted the chance to go ahead in the 20th minute after Anfernee Dijksteel slipped and brought down Pogba in the box.
Referee Anthony Taylor pointed to the spot and Cristiano Ronaldo fired his right-footed effort wide of the left-hand post in front of the elated Boro support.
The Red Devils did not take long to break the deadlock.
Pogba intercepted and Bruno Fernandes fired over to Sancho on the left, with the summer signing showing nice footwork before hitting a drive that went in via an Isaiah Jones deflection.
United went into the break 1-0 up but there was bad news before half-time for fans as it was announced no food or drink would be sold on the Old Trafford concourses due to a “technical fault”.
Chants calling for the Glazer family, the club’s owners, swiftly followed.
Lifelong United fan Matt Crooks silenced the Old Trafford faithful as he made it 1-1.
Duncan Watmore handled before crossing for the midfielder to score, but the 64th-minute goal was allowed to stand.
Fernandes hit a post with the goal at his mercy in the 72nd minute as United pushed to go back ahead.
Despite United’s dominance, the match went to extra time at Old Trafford as Boro kept the scoreline at 1-1 after 90 minutes.
The game went to a penalty shoot-out after no further goals were scored in extra time.
Middlesbrough knocked United out of the FA Cup after winning the shoot-out 8-7, with Elanga skying the decisive penalty.
More to follow…
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