Manchester United crashed out of the FA Cup as Championship side Middlesbrough came from behind at Old Trafford and then emerged victorious in a nail-biting 16-shot penalty shootout.

It was only the second time in 11 meetings with Premier League opposition that Middlesbrough had progressed, following on from their equally surprising success at Manchester City in 2015.

United will complain about Middlesbrough’s controversial equaliser, scored by Matt Crooks, who tapped home despite Duncan Watmore clearly handling in the build-up.

However, they only had themselves to blame after failing to take numerous chances in a game where they had 30 shots at goal, the clearest of which came when Cristiano Ronaldo missed a penalty in the first half.

Jadon Sancho seemed to have put United on the road to the last 16 when he marked his FA Cup debut with a goal.

Instead, United’s most realistic chance of silverware has now disappeared.

The draw for the FA Cup fifth round will take place at 11:40 GMT on Sunday.

A moment of controversy

Who could have known an alteration to the handball rule would have such an impact on the outcome of this match?

Following a revision of the interpretation of the rule by IFAB during the summer, accidental handball is only penalised if the player in question then scores a goal.

So, although the ball clearly hit Watmore’s hand before he lobbed the decisive pass to Crooks, referee Anthony Taylor deemed it to be accidental, as the ball had flicked up off the Middlesbrough man’s body. This was subsequently checked by VAR Stuart Attwell, who endorsed Taylor’s view.

Given Ralf Rangnick had spent the previous few seconds tapping his arm and did so again as Taylor pointed to the centre circle, desperately looking round for someone to appeal to, it is fair to assume United’s interim manager did not agree with the officials.

A sorry night for Man Utd

United only had themselves to blame for the mess they ended up in.

Their profligacy started in the opening two minutes, a horrendous mix-up in the Boro defence ending with Sancho lobbing against the bar from the edge of the area before Bruno Fernandes fired over when it seemed easier to score.

Fernandes did not have a great night. He thought he was offside when, unmarked, he headed over from eight yards. But TV replays showed the goal would have stood. That miss was about the same level as when he hit the post in the second half with the goal at his mercy.

And then there was Ronaldo, whose night was summed up deep into extra time when United were trying to counter and he attempted a 10-yard pass to Fred, which he overhit straight to an opponent, forcing the Brazilian to make a crude challenge at the expense of a yellow card to ensure the home goal did not come under threat.

The noise when Ronaldo missed his penalty was louder than when Boro equalised.

In a game of fine margins, the Portuguese’s attempt to find the bottom corner after Anfernee Dijksteel had slipped and fallen into Paul Pogba was only out by a couple of inches. It was enough though.

Sancho did find the net with the aid of a deflection but United’s wastefulness kept the visitors in the game, meaning the VAR controversy really mattered and by the end it was Dean Henderson who was needed to ensure the match went to penalties when he blocked Aaron Connolly’s goalbound effort.

And if United’s evening was not miserable enough on the pitch, they suffered embarrassment off it as well, when a technical fault meant no food or beverages could be provided at half-time, triggering chants of ‘we want Glazers out’ from a section of the United support.

Repeat job for Wilder

This was not the first time recently Wilder had left Old Trafford as a winner.

In January 2021, Sheffield United were fancied even less than Middlesbrough were tonight and secured a 2-1 win.

On this occasion, though Middlesbrough’s defending was poor initially, they grew into the game.

Goalkeeper Joe Lumley recovered from a couple of early errors and got his positioning right to make some decisive saves.

The introduction of Watmore, a local boy who started his career at nearby Altrincham, gave Middlesbrough’s attack a focus and it was a bitter irony that United academy product Crooks should score against the club he supported as a boy.

There was confidence in the visitors’ penalties too, with Henderson only coming close to stopping one, Middlesbrough’s second, from Martin Payero, which went under his body.