Middlesbrough shocked Manchester United in an 8-7 penalty shootout win to advance from the FA Cup fourth round at Old Trafford on Friday night after 120 minutes of regular and extra time ended in a 1-1 draw.

The hosts had a golden opportunity to open the scoring just before the 20-minute mark when Paul Pogba was brought down in the area, but Cristiano Ronaldo flashed his spot kick wide and the score remained tied.

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Jadon Sancho made amends shortly after, firing a shot past Middlesbrough's Joe Lumley from a tight angle after settling a long pass over the top of the defence to give Ralf Rangnick's side a lead they would take into half-time.

Middlesbrough levelled the score in the 64th minute when Matt Crooks slid in at the far post and redirected a looping ball from Duncan Watmore into the back of the Man United net to make it 1-1.

Watmore appeared to control the ball with his hand before setting up Crooks, but the referee did not blow his whistle and VAR saw no clear error so the goal stood.

"Incredibly disappointed, we should have won and killed off the game in the first half," Rangnick said after the match. "Crossbar, post, missed penalty and numerous chances. It should have been 2-0 or 3-0.

"We conceded a goal which I don't understand why it stood. He controlled it with his hand. In the moment when they scored, it was clear that VAR would not allow this goal to stand. We were not well positioned in that moment, too open and allowed them the counter, we should have won the game."

Bruno Fernandes somehow struck the post with the goal gaping soon after the Middlesbrough leveller and the match went to extra time and then to a shootout.

Both sides hit their first seven spot kicks, but after Lee Peltier Boro's eighth, Manchester United's Anthony Elanga skied his over the bar to hand the visitors a famous FA Cup win.

Rangnick said of the decisive miss: "Anthony Elanga, anyone can imagine how he is, he is shattered and absolutely disappointed."

It was a hammer blow for United, who will wonder how they will not be in the hat for the fifth round after having 30 goal attempts to Boro's six.

"The FA Cup is alive and kicking, especially in Middlesbrough," said Boro manager Chris Wilder, whose Sheffield United team won at Old Trafford in the Premier League last season. "I told the players it was all about making memories."