FA Cup: Middlesbrough stun Old Trafford with penalty shootout win

Manchester United's Cristiano Ronaldo missed a penalty in normal time. Picture: Martin Rickett

Man United 1 Middlesbrough 1

(Middlesbrough win 8-7 on penalties)

Manchester United’s troubles mounted as they exited the FA Cup fourth round to Championship side Middlesbrough in a penalty shoot-out although it was a spot kick miss in normal time — by Cristiano Ronaldo, no less — that contributed to their downfall.

After Jadon Sancho and Matt Crooks traded goals, and extra-time failed to produce another, young substitute Anthony Elanga was the culprit in the shoot-out, placing the 16th kick of the competition high over the visitors’ goal.

United thus lost 8-7 although it was events of the first 90 minutes of the evening that sealed their fate — especially the penalty miss by Ronaldo who, inevitably, made no mistake when he was one of the successful United takers in the shoot-out.

Crooks struck a shock equalising goal after 64 minutes which will rank among the most controversial in the competition this season, despite VAR having the chance to over-turn referee Anthony Taylor’s potential error.

Isaiah Jones swung over a cross and, with the United defence in disarray, Duncan Watmore controlled the ball, clearly using his outstretched hand in the process before hooking the ball towards the far post.

Crooks arrived at full speed and turned the ball into the open goal — prompting protests from United players and coaches which somehow went ignored.

New rules introduced by the International Football Association Board last summer now allow handball in the build-up to such a goal but only if accidental - and whether or not Watmore’s infringement was accidental was open to debate.

Still, United only had themselves to blame for terrible defending and a long catalogue of misses.

After the equaliser, there were still openings for the Premier League side, with Marcus Rashford drawing a fine save from Joe Lumley and Bruno Fernandes guilty of an astonishing miss.

Lumley’s poor clearance was intercepted by Bruno who, with the goal virtually empty, struck the left-hand post from the edge of the area, a chance so routine that he appeared to be celebrating as he struck the ball.

But the penalty miss by Ronaldo, who turns 37 today (SAT), was the moment that would prove most costly after 20 minutes.

Anfernee Dijksteel’s trip on the returning Paul Pogba, back for the first tine since November, had left Taylor with no choice but to award a penalty and United the chance to take the lead. Ronaldo looked composed enough as he addressed the ball, and struck it powerfully, but well wide to the left of the Boro goal.

Fortunately, for Ronaldo and his manager, it took Sancho barely five minutes to relieve any potential embarrassment with ban excellently taken opening goal.

Pogba won an important interception in the centre circle and allowed Bruno Fernandes to loft a superb pass into the path of the England winger. With Jones allowing him too much space, Sancho struck a powerful effort across Lumley and in at the far post.

The penalty miss had been symptomatic of a rare “off” night by Ronaldo, in terms of his finishing at least, although this was one of the more ambitious and competent attacking performances his side had put together on Ralf Rangnick’s watch to date.

United could have made the ideal start with a goal after one minute after Lumley and Dael Fry tangled with each other in trying to deal with a Luke Shaw centre with the keeper palming the ball to Ronaldo. The Portuguese squared the ball for Sancho whose well-weighted effort struck the cross-bar before the ball fell to Bruno Fernandes who steered a difficult chance wide from the rebound.

There were at least two more glorious chances for Ronaldo; first on 28 minutes when he sprinted purposefully down the inside left channel and rolled his shot inches wide of the far post.

And, later, a superb ball from Bruno put Ronaldo clean through on goal only for the legendary striker to hit the ball directly at Lumley, who had judged his angles well.

Rashford had the ball in the net again, after half an hour, but saw his effort ruled out for offside and the England forward hit one shot over and another straight at the keeper as United applied late first half pressure from corners.

After the restart, Sancho continued his impressive night’s work, chasing Shaw’s through ball and offering up a perfect delivery which Rashford struck wide with a wild effort from eight yards.

Ronaldo’s frustrations continued, as Rashford pulled the ball back for him and the striker hit a powerful effort into the side-netting but there was a reminder that Chris Wilder’s side posed a threat, Crooks effort tipped over.

Man United (4-2-3-1): Henderson 6; Dalot 5, Varane 7 (Jones 90, 6), Maguire 5, Shaw 6; Pogba 7 (Fred 81, 6), McTominay 6; Rashford 7 (Elanga 81, 5), Fernandes 6, Sancho 8 (Mata 99, 5); Ronaldo 5. Substitutes (not used) Grant, Heaton, Wan-Bissaka, Matic, Mejbri.

Middlesbrough (3-5-2): Lumley 7; Dijksteel 5, Fry 5, McNair 6; Jones 7 (Bamba 118), Crooks 8 (Payero 78, 5), Howson 7, Tavernier 7, Taylor 6 (Peltier 90, 5); Sporar 6 (Connolly 90, 6), Balogun 5 (Watmore 61, 7). Substitutes (not used) Wood, Daniels, Coburn, Boyd-Munce.

Referee: A Taylor 5