Middlesbrough FC knock out Manchester United on penalties in stunning Cup upset

From Middlesbrough's FA Cup victory at a snow-covered Ayresome Park in the early 70s to a teenage Ryan Giggs breaking Teesside hearts in the League Cup semi-final second leg at Old Trafford in 1992.

There was Gary Pallister's clearance off the line against his old club in that very same game alongside Peter Schmeichel's stupendous save to deny Willie Falconer.

Not forgetting Wayne Rooney's wonder goals in 2005, while Boro's previous cup visit to United in 2016 produced a dazzling occasion when a 10,000 strong travelling support lit up the Theatre of Dreams in support of sacked steelworkers and saw their side memorably triumph on penalties.

Spot-kicks were again needed to separate these sides after the game ended 1-1 after extra-time and again Boro progressed in stunning fashion as they became the first EFL side to knock United out of the FA Cup on home soil since Leeds United in January 2010.

Fifteen penalties were converted before Anthony Elanga ballooned his effort into the Stretford End. It was a stunner for United.

Utterly dominant for almost an hour, United - who shrugged aside a spot-kick miss from Cristiano Ronaldo of all people in his first FA Cup appearance in 13 years - unfathomably failed to add to Jadon Sancho's 25th-minute opener - and were left stunned by a moment of huge controversy on 64 minutes as the game turned.

It came when boyhood Red Devils fan Matt Crooks - who came through the United youth ranks - tucked away an equaliser after a clear, but accidental handball from another player formerly on the hosts' books in substitute Duncan Watmore.

The goal was allowed to stand due to changes in handball laws this season. Watmore was not the player who scored with Crooks turning in his lob over Dean Henderson into an unguarded goal. So the strike was permitted.

It turned what had hitherto been a routine occasion into a proper cup tie in front of 9,700 jubilant Boro supporters.

Earlier, their side had palpably struggled to cope with their tempo and crisp interplay which was certainly of a higher standard than they usually face in the Championship.

Inspection of the teamsheet quickly pointed to Ralf Rangwick’s intent, with the overwhelming majority of big-hitters there including Paul Pogba, making his first appearance in three months.

Chris Wilder spoke beforehand about the importance of his players not turning up for sight-seeing and with their autograph books in toe. He was here for business - yet the hosts were also deadly serious.

For his part, Wilder was entitled to be grateful that the scoreline was kind to his side at the break, with the Teessiders trailing by just one goal.

An early opener which would have ripped Boro’s game-plan to shreds could - and probably should - have arrived.

Wilder’s side also had the major reprieve of Ronaldo’s surprise miss after Anfernee Dijksteel's panicky foul on Pogba. But it was a night when United’s opener had an air of inevitability about it.

Sancho got away from Isaiah Jones from Bruno Fernandes’ pass with Paddy McNair sloppy in playing the winger onside, compounding Crooks’s initial error in giving the ball away.

The £73m summer signing’s left-footed finish was clinical as he registered his first goal at Old Trafford.

Boro were almost truly up against it from the off when Joe Lumley coughed up the ball on the edge of his box and was left in no-man’s land. Sancho’s lob hit the bar and Fernandes put the rebound wide.

Ronaldo’s overhead kick, not quite in the sweet spot, was held by Lumley before the collector’s item of a penalty miss from CR7.

Sancho’s strike ensured a lead that the hosts merited before an offside flag spared Lumley’s blushes after Marcus Rashford's shot crept under him.

Thankfully for his and Boro’s sake, there was no further damage before the interval provided respite.

The onus was on Boro to give their illustrious hosts something to think about, while breaking up United’s rhythm more successfully than they did in the opening half.

Initially, it was more of the same - with Rashford and Ronaldo mercifully missing chances to seal it. Then it somehow changed.

After going close to punishing United’s profligacy when his rising strike was splendidly tipped over at his near post by Dean Henderson, Crooks had his moment amid some controversy.

Quite how Fernandes hit the post instead of converting after another wretched error from Lumley is anyone’s guess as Boro secured a minor victory by securing extra time and the night belonged to Boro.

Manchester United: Henderson; Dalot, Varane (P Jones 90), Maguire, Shaw; McTominay, Pogba (Fred 82); Rashford (Elanga 82), Fernandes, Sancho (Mata 100); Ronaldo. Substitutes unused: Grant, Heaton, Wan-Bissaka, Matic, Mejbri.

Middlesbrough: Lumley; Dijksteel, Fry, McNair; I Jones (Bamba 118), Crooks (Payero 79), Howson, Tavernier, Taylor (Peltier 90); Sporar (Connolly 90), Balogun (Watmore 62). Substitutes unused: Daniels, Wood, Coburn, Boyd-Munce.

Referee: A Taylor (Cheshire).

Attendance: 71,871.