Even by Manchester United’s strange modern standards this was a bizarre way to lose.
A missed Cristiano Ronaldo penalty in the first half of regulation play, two shots against the frame of the goal and then the concession of an equaliser that said everything about the ludicrous nature of the modern handball law. By the end of extra-time United had mustered 30 shots to Middlesbrough’s six.
But the fact that boyhood United fan Matt Crooks had been able to equalise Jadon Sancho’s first half goal after what looked like a clear use of the arm by Duncan Watmore in the 64th minute meant that this remarkable FA Cup tie ended up going to penalties.
Manchester United (above) were knocked out of the FA Cup by Middlesbrough on penalties on Friday evening
Middlesbrough (above) managed to beat the Red Devils 8-7 on penalties at Old Trafford after the game ended 1-1
And when it did, Middlesbrough magnificently and bravely won it on sudden death.
In terms of the chronology of the shoot-out, Paddy McNair, Martin Payero, Jonny Howson, Marcus Tavernier and Sol Bamba all scored for Middlesbrough while Juan Mata, Harry Maguire, Fred, Ronaldo and Bruno Fernandes for United made it a perfect ten in the regulation round.
But once Watmore, Dael Fry and Lee Peltier had scored for Chris Wilder’s team and Scott McTominay and Diogo Dalot had done likewise in the sudden death section for United, it was a slash over the bar by young Anthony Elanga that lost it for Ralf Rangnick’s team and sent Middlesbrough through.
There will be much focus now on the handball for the equaliser and the number of chances wasted by Rangnick’s enduringly hapless team team. But Middlesbrough grew braver and more assured as this night wore on and had not been threatened in extra time.
As for their penalties, they were perfect. All eight of them. It takes nerve to execute like that in front of the Stretford End and the manner in which Wilder’s players stared down the task will stand them in good stead ahead of what may yet be a promotion push on Teesside.
Manchester United’s star striker Cristiano Ronaldo (above) missed a penalty in the first half of the game to make it 1-0
However, former Dortmund-man Jadon Sancho (right) scored in the 25th minute to put Manchester United ahead
As for United, this was about regret. Whether the fact they played pretty well for the first hour will console or irritate them, we can only imagine.
But with four months of the season left, United are relevant now in only one competition – the Champions League – and that says everything for their struggles.
By the end of extra-time, United had on the field players signed by five different managers. That points at a muddle. Equally, this is a game that should have been over after 45 minutes.
United – with Paul Pogba back – hit the bar through Sancho in the second minute and Fernandes lifted the rebound over.
That set the tone for the direction of the traffic but also for the manner in which Rangnick’s team approached the task of scoring goals.
Ronaldo struck a penalty wide in the 19th minute but Sancho scored across goalkeeper Joe Lumley six minutes later.
Middlesbrough’s offside line at this stage resembled a bolt of lightening and they were not, frankly, in the game.
A Rashford shot was held by Lumley just before half-time while Ronaldo also came close. Early in the second period, meanwhile, Rashford was wasteful at the far post after Sancho set him up well and then Ronaldo whipped a shot in to the side netting.
Teams that miss chances are often vulnerable but it didn’t really feel that way here. Indeed, the result did not seem in any doubt until suddenly it was.
Middlesbrough had enjoyed marginally more of the play as the hour mark came and went but even so it was a surprise to see Isaiah Jones’ cross reach Duncan Watmore unmarked at the far post.
Middlesbrough midfielder Matt Crooks then scored a controversial goal in the second half to level the score and make it 1-1
The goal was controversial as the ball came off Duncan Watmore’s hand before he played the cross into the goal scorer
Watmore, fresh on the field as a substitute, seemed surprised also as his first touch was so poor that it deflected the ball up on to his outstretched arm. As he poked the ball over Dean Henderson for Crooks to bundle in from a yard, a whistle seemed certain to come.
But the amended IFAB rules implemented last summer say accidental handball will only be penalised if the same player goes on to score. Watmore didn’t do so and that meant the goal withstood a VAR review.
It’s a stupid rule but it’s a rule nevertheless. So Middlesbrough were back in the game and over the course of the next hour or so, they remained so.
United had other chances. Fernandes struck a post after goalkeeper Lumley made a mess of a clearance and then Rashford worked him on the other side of his goal. Late in the game, meanwhile, substitute Elanga was offered two headed chances and missed both.
Worse was to come for the 19-year-old and his penalty certainly was a dreadful one. But this was a night about collective problems that refuse to go away.
At half-time, an electricity problem meant that United could not even sell any pies. At Old Trafford, a feeling of high farce endures.
It was Manchester United starlet Anthony Elanga missed his sudden death penalty to knock Ralf Rangnick’s side out
Scroll down to re-live the minute-by-minute action as it happened with Sportsmail
Thank you for following tonight’s coverage of Middlesbrough’s victory over Manchester United in the FA Cup.
This will be Manchester United’s fifth season without a trophy!
MANCHESTER UNITED ARE ELIMINATED FROM THE FA CUP
Elanga MISSES – firing it well over the bar!
Peltier scores for the Boro. 8-7
Dalot scores for Unitetd. 7-7
Fry scores for the Boro. 7-6
McTominay scores for United. 6-6
Watmore scores for the Boro. 6-5
Sudden death!
Fernandes scores for United. 5-5
Sol Bamba scores for the Boro. 4-5
Ronaldo scores for United. 4-4
Tavernier scores for the Boro. 4-3
Fred scores for United 3-3
Howson scores for Boro -3-2
Maguire scores for United. 2-2
Payero scores for Boro 2-1
Mata scores. 1-1
McNair scores. 1-0
Boro to take the first spot kick…Paddy McNair vs Dean Henderson
122mins: What a performance by Middlesbrough. Penalties here we come.
121mins: Two minutes of additional time have been added but I think we are set for penalties. It doesn’t look like a goal is coming any time soon
FYI: Manchester United have lost six of their last seven penalty shootouts… not ideal for the Red Devils
119mins: No…
Maguire manages to miss the ball at the back post and it’s clear away from the goal.
118mins: United corner…could this be it?
117mins: Manchester United fans are furious…the Boro players are running down the clock at every opportunity they get.
116mins: 3 and a half minutes before penalties – Manchester United are going to have to make something happen…and quickly.
115mins: What a chance for Middlesbrough! That was a real threat to the Manchester United goal! However, Henderson denied Connolly at the back-post.
114mins: Fred is awarded a yellow card are clashing with Connolly
112mins: Manchester United clear the corner with ease. 7 and a half minutes to go. Penalties are looming.
111mins: Jones gives away a free-kick in a dangerous area – giving Middlesbrough the chance to fire it in from the left-side of the box. The ball is swung in to the back post. Maguire has to deal with it and heads it out for a corner.
109mins: United are looking to make crosses into the box to maximise Ronaldo’s aerial excellence. However, the United star has been struggling this evening so it may be time to change things up…
106mins: That looked like it could have been it for United! Fernandes came close to making it 2-1 after getting on the end of Dalot’s cross but Lumley made a wonderful reactionary save.
However, I think the United midfielder could have been offside…
Here we go – the final 15 minutes before penalties has started.
United physios spent the short break rubbing deep heat into Fernandes’ back. Rangnick will want him to stay on the pitch in case the game goes to spot kicks.
Just 15 minutes to go. We’re still level at half-time of extra-time
106mins: Wonderful build-up play from Manchester United – pinging it around the edge of the box before finding Fred. However, the substitute fired it so far wide he even held his hands up to apologies to the fans.
103mins: The Boro sustain some serious pressure but manage to hold off Ronaldo as he charges in on goal.
99mins: Sancho is finally replaced by Mata – probably about nine minutes too late though.
90+7mins: Fernandes is now down, asking for medical attention from the physios after getting a knee in the back.
After receiving treatment on the pitch, Fernandes is back on his feet.
90+6miins: Great chance for the Boro but it wasn’t meant to be! Watmore drives down the right wing before firing across the mouth of the goal.
90+4mins: Play has been stopped again to change the ball. That is the third time this game they’ve had to swap the ball out.
90+3mins: I can’t believe they don’t have a sub ready for Sancho? The physio has just come on, rubbed him down and sent him back onto the pitch.
Must be cramp?
90+2mins: Sancho is reaching for both of his hamstrings on the side of the pitch, Maguire puts the ball out of play.
Makes you think…could they not have used Lingard tonight?
Here we go! Extra-time is underway at Old Trafford. Jadon Sancho is still on the pitch despite raising concerns over his hamstring. Meanwhile, Varane is off and Jones is on.
Aaron Connolly and Lee Peltier have also been brought on for Middlesbrough.
The final whistle goes – we’re in for an extra 30minutes ladies and gentlemen! Sit tight, we’ll be bringing you the minute by minute coverage shortly
90+1mins: Chance for Elanga! Shaw sends the ball into the substitute – who found himself in front of goal. However, he headed the ball straight at the goalkeeper.
90mins: Four minutes of additional time has been added…but will it be enough to avoid extra-time? I’m not convinced considering the chances they’ve missed so far.
89mins: United have had more chances than I’ve had hot meals! It’s unbelievable they haven’t scored another yet…
Their latest chance saw Fred attempt to slide Fernandes into the box. However, his pass was intercepted.
86mins: With just four minutes to go, frustrations in the United camp are starting to appear. They should have wrapped this up a long time ago…
82mins: Former Red Devils Paddy McNair is down receiving medical treatment while Manchester United make their changes,
Once the substitutions are made, McNair rises to his feet and carries on.
82mins: Rashford comes off for Elanga, while Pogba comes for Fred. Will these substitutions be enough to inspire a goal for United? Only time will tell…
80mins: Manchester United get another corner.. Luke Shaw steps up. He plays it long towards the back post. However, there was a bit little too much on it for Pogba- who tried to chest it down before being dispossessed.
78mins: Middlesbrough goal scorer Crooks has been substituted for Payero. Meanwhile, Fred and Elanga are getting ready to come on for Manchester United.
75mins: It’s only a matter of time before Manchester United score again. Surely they have to put in one of these chances!?
The Red Devils will be eager to avoid extra-time and possibly penalties.
72mins: Fernandes hits the post!! How did he miss that!?
Fernandes becomes the latest Manchester United player to miss a goal scoring opportunity after pressing high to win the ball on the edge of the box.
He aimed for the bottom left corner but he drags it too far wide – hitting the post as a result.
70mins: Manchester United are under pressure now…but they are keeping their cool. The Red Devils look confident.
GOAL! VAR have ruled that the goal will stand – meaning the score stands a 1-1.
If I was a Manchester United defender…I would be fuming with that decision…
64mins: Crooks levels the score for Middlesbrough! However, VAR are checking for a possible handball as Duncan Watmore touches the ball in the box before crossing it to Crooks at the back-post to tap-in.
59mins: Dean Henderson is forced to make his first save of the night – palming Crooks’ effort over the bar. As a result Middlesbrough got their first corner of the evening. However, Manchester United collected the ball comfortably from the near post.
57mins: It’s a frustrating night for Ronaldo. Sancho cut into the middle from the left side and slipped Ronaldo the ball inside the box. Ronaldo took the ball around Lumley but cuts off the angle to shoot, Therefore, he tried to back heel it into the box but it deflected off his standing leg and went out for a goal kick.
54mins: Ronaldo hits the side netting.
It was Rashford who drove down the right wing and dragged the ball back for Ronaldo – who fired it wide.
Manchester United are knocking on the door again.
53mins: Rashford misses another chance. How has he not scored that?! He’s even questioning himself.
Sancho works his way into the box and beats Dijksteel before sending the ball to the back post. Rashford arrives on time (with plenty of time) but put the ball over the bar.
50mins: The Boro are looking to challenge the Manchester United backline with through balls over the top. However, Shaw has been doing well to head them away.
48mins: United get another opportunity – this time it falls to Rashford. Dalot played the ball into the box for Rashford but the England international was beaten to it by Paddy McNair.
47mins: Manchester United broke away on the counter – with a through ball almost finding Ronaldo. However, Lumley was quick out to lump it away.
46mins: Chance for the Boro.
Wilder’s men came flying out of the blocks after the break. They started the second half with a chance that could have levelled the scores. They played the ball past the two United full-backs but Dalotmanaged to clear the ball.
The second half is under way!
And just the like that…it’s halftime! Manchester United head into the game 1-0 up thanks to Jadon Sancho.
45mins: Fernandes has what could be the final chance of the half – heading it straight into the arms of Boro goalkeeper Lumley.
41mins: Pogba shown a yellow card for a foul in the middle of the park. He lost the ball to Marcus Tavernier and tried to win it back immediately. However, he caught the Boro playe’s leg – taking him down.
41mins: Chance for Rashford. Shaw played the ball into the box for Fernandes let it roll through to Rashford. The England international shot but his effort was deflected behind.
Rashford also got a second chance – Sancho dribbled the ball into the box and played it to Rashford at the edge of the box. He fired it straight at Lumley.
37mins: Manchester United get another corner. However, they do little with it once again.
Shaw was hoping to find Maguire with his cross but Dael Fry beat him in the air and headed the ball out of danger.
35miins: Another good effort for the Boro – who were able counter after Ronaldo had another shot blocked by Lumley. It was Jonny Howson who brought the ball up and threatened the United defence.
Howson found, Balogun – who ran inside of Varane – before shooting wide.
32mins: Good chance for Middlesbrough! However, United were then able to catch the Boro on the counter-attack. But, there was no outcome as Ronaldo fired an effort straight at Lumley.
30mins: Rashford finds the back of the net but NO goal for the England international as he is deemed offside. Should the goal have stood, it would have been a lucky one! Rashford fired it straight down the middle at the keeper but it somehow went in.
26mins: Another close chance for Manchester United – however, it was not meant to be. Fernandes fired it across the box for Ronaldo but it was just out of reach and turned out to be an easy recovery for the keeper.
25min: Manchester United take the lead (finally) thanks to Jadon Sancho.
The goal came after Paul Pogba intercepted a pass in midfield and played it to Bruno Fernandes. Fernandes saw Sancho running into the box and floated the ball into him. Sancho took it down, beat Isaiah Jones then fired it into the far bottom corner!
23mins: Another effort for Manchester United but Bruno Fernandes fires his volley over from close range.
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19mins: Ronaldo steps up to take Manchester United’s penalty. However, the goal scorer put the ball wide! Ronaldo turned around and looked down at the penalty spot as if to blame the pitch. The score remains 0-0
Manchester United awarded a penalty.
Luke Shaw plays Paul Pogba through on goal but Anfernee Dijksteel took the Frenchman down. As a result, United were awarded a spot kick.
16mins: Manchester United get their first corner of the game but do little with it.
15mins: Isaiah Jones wins the ball off Bruno Fernandes in his own half and drives through the midfield. However, United quickly recovered and won the ball back thanks to a sliding tackle from Pogba.
10mins: Maguire played the ball into McTominay in the middle of the pitch. He controlled it and gives it Ronaldo. Ronaldo played it to Dalot – who sprinted into space on the right side.
Dalot cut inside and gave the ball back to Ronaldo. He flicked it up and attempted to volley it. However, it didn’t come off.
7mins: Fernandes has made runs straight through the heart of the Boro defence four times in the first 7mins of the game.
6mins: Good chance for Manchester United. Marcus Rashford carried the ball inside from the right wing and gave it to Paul Pogba.
The Frenchman then found Bruno Fernandes inside the box before playing in Sancho. Sancho then passed it on to Luke Shaw – who made an overlapping running. The left-back floated a cross into the box for Cristiano Ronaldo- who meets it with an overhead kick.
However, it was an easy save.
4mins: United win the ball back and send it to Scott McTominay who is immediately put under pressure but the midfielder. However, he does well to hold off the Boro players and ultimately wins a free-kick.
3mins: Luke Shaw lost possession in midfield and had to work hard to sprint back to the edge of his own penalty area.
2mins: Manchester United off to a flying start – hitting the bar in the second minute of the game. The keeper went a loose ball but Dael Fry got in his way causing him to fumble it.
As a result, the ball fell Ronaldo who played in on to Sancho outside the box. Sancho then chipped it over the Boro defence onto the bar
Both manager lay a wreath at Old Trafford ahead of the fourth round FA Cup tie to to commemorate the anniversary of the Munich Air Disaster. Shortly after, play got underway
He said: ‘This is another opportunity to try and get a result, for the players and everybody at the club. We don’t want the evening to pass us by. We want to make it dangerous for Manchester United.
‘We have to have a strategy. When we have the chance to play we have to be progressive and cause them issues. We have to play as a team, everyone has a job to do.
‘We don’t want to sit back and sit on the crossbar for 95 minutes, otherwise the inevitable will happen.’
We are just 10 minutes away from the start of the game. The warm-ups are done and the teams back in the changing rooms.
Tonight provides an opportunity for Manchester United to put a marker down. Pogba is returning to the squad, Ronaldo is starting alongside Fernandes, Rashford, Sancho…
Questions will be asked if they don’t walk away with a result…
He said: I have no control over that (speculation). I made it clear I would like to go back in football as manager one day but the club has to want you and you have to want the club and the contract has be right. Let’s see what takes shape over the next few days.’
Rangnick has told Pogba that he has to earn a regular place in the Manchester United starting XI.
‘It depends on the level of performance he shows tonight,’ Rangnick told MUTV when asked if the Frenchman could play an important role now he’s fit again.
‘He was good in training, he performed well and that’s why I decided to play him from the start.’
United XI: Henderson, Dalot, Varane, Maguire, Shaw, McTominay, Pogba, Fernandes, Sancho, Rashford, Ronaldo.
Subs: Grant, Heaton, Jones, Wan-Bissaka, Fred, Hannibal, Mata, Matic, Elanga.
Middlesbrough XI: Lumley, Dijksteel, Fry, McNair, Jones, Crooks, Howson, Tavernier, Taylor, Balogun, Sporar
Subs: Daniels, Boyd-Munce, Payero, Peltier, Wood, Watmore, Bamba, Connolly, Coburn
Ralf Rangnick has shared his reasoning for starting Pogba and Henderson tonight.
‘[Pogba] was good in training, he performed well in training and that’s why we decided to play him from the start.
‘With Dean [Henderson] we have a fantastic goalkeeper. His training performances since I arrived have been outstanding and that’s why I decided to give him this game in front of a sold out Old Trafford stadium. He more than deserved that.’
Middlesborough defender Paddy McNair is making e his return to Old Trafford this evening. McNair started his playing career with United’s youth academy, joining at 16, and was tipped the next Gary Neville after making his senior debut aged 19 in 2014.
However, McNair fell down the United pecking order and left for Sunderland in 2016.
Folarin Balogun will make his first start since joining the club on loan from Arsenal earlier this month. The youngster put pen to paper on a temporary move to the Championship side after undergoing a medical at the club.
Balogun is in desperate need of first-team football after making just four appearances all season, with his last Premier League outing coming back in August.
Middlesbrough XI: Lumley, Dijksteel, Fry, McNair, Jones, Crooks, Howson, Tavernier, Taylor, Balogun, Sporar
Subs: Daniels, Hall, Payero, Peltier, Wood, Watmore, Bamba, Connolly, Coburn
It is good to see Hannibal Mejbri in the squad but it is disappointing not to see more youngsters being handed an opportunity considering the club pride’s itself on developing the next generation. Do United really need two keepers on the bench?
United XI: Henderson, Dalot, Varane, Maguire, Shaw, McTominay, Pogba, Fernandes, Sancho, Rashford, Ronaldo.
Subs: Grant, Heaton, Jones, Wan-Bissaka, Fred, Hannibal, Mata, Matic, Elanga.
United will mark the 64th anniversary of the Munich Air Disaster. Rangnick will lay a wreath at Old Trafford ahead of the fourth round FA Cup tie with Middlesbrough.
The Red Devils will also wear black armbands for the fixture.
‘This is our closest game to the anniversary of the Munich Air Disaster and, as is customary, the club will be marking the occasion ahead of kick-off,’ Rangnick said.’“I have always admired how this club pays tribute every year to such a major incident in its history.
‘It is important that this tradition always continues because it is such a big part of the Manchester United story. I hope that we are also able to mark the occasion with an important victory this evening.’
As it stands, Phil Jones is one of only three centre backs available to Rangnick at the moment and he’d rather play him tonight than risk either Maguire or Varane getting injured ahead of their clash with Burnley on Tuesday.
Manchester United’s interim manager shared his thoughts on the competition.
‘This is a great competition with so much history, and winning a trophy is always a great boost for any group of players,” he said. “For this squad, the first trophy they win together can be a springboard for a lot more success in the future.’
United will be without a host of key players tonight. Ralf Rangnick ruled five out at his press conference on Thursday.
‘There are still a couple of players missing out. Edi Cavani will only return at the weekend, he contacted me a week ago and asked if he could have two more days at home. I allowed him because I knew he couldn’t be in starting XI anyway with jet lag and only coming back today or last night, so he won’t be part of the group.
‘Victor Lindelof has been ill the whole week and not training, so he will miss out on tomorrow’s game. The same is true with Jesse, he asked me and the club if we could give him a couple of days off just to clear up his mind. He will be back in the group next Monday, back for training and then be part of the regular squad again.
‘Eric Bailly came back yesterday, he has some problems, a swollen ankle, and will not be part of the squad tomorrow. All of the other players will be available.’
Speaking ahead of the game, Wilder said: ‘They’ve got some fabulous individuals and they can hurt you – but hurt three-quarters of the Premier League, if not more, and in Europe as well. They have a huge array of talent to choose from,” he said before the game.
“Their team sheet will come in the dressing room and it’ll be De Gea, Varane, Harry Maguire… let’s not crumble in that process!
“But it’s not a sightseeing tour from our players, it’s not a shirt-swapping situation. I don’t want people to go into Old Trafford and enjoy the visit. If they want a shirt, do it in the changing rooms after. We don’t want to be looking at them all fuzzy-eyed. They are up against a competitor.”
Scott McTominay has the potential to stand out tonight. He has scored three of Manchester United’s last seven FA Cup goals.
Those included 1-0 victories at Old Trafford – v Watford (Jan 2021), West Ham (Feb 2021) and Aston Villa.
Manchester United have a good track record against Middlesborough. Following their 4-1 defeat in 2005, United have have gone unbeaten in their last 13 matches with Middlesbrough across all competitions.
Additionally, United have won 28 of their last 31 home FA Cup matches against sides from a lower division, including each of their last eight without conceding a goal.
The Manchester United squad were seen arriving at The Hyatt Hotel on Friday afternoon to prepare for tonight’s FA Cup match against Middlesbrough at Old Trafford.
Among those seen getting on the team bus were: Dean Henderson, Tom Heaton, Lee Grant; Diogo Dalot, Luke Shaw, Harry Maguire, Aaron Wan-Bissaka, Phil Jones, Raphael Varane; Nemanja Matic, Scott McTominay, Bruno Fernandes, Fred, Paul Pogba, Juan Mata, Hannibal Mejbri; Jadon Sancho, Anthony Elanga, Cristiano Ronaldo, Marcus Rashford.
Manchester United have been handed a boost for the game as Paul Pogba is back in the matchday squad for the first time since November.
The 28-year-old – who sustained a thigh injury with France in November – has been out of action for over two months.
The last time he pulled on a Manchester United shirt was against Atalanta in the Champions League. While his last domestic appearance came against Liverpool.
Ralf Rangnick’s Manchester United side have gone 13 days without a game due to the one-off international break. Therefore, the players should be rested and ready to go for tonight’s fixture.
Hello and welcome to Sportsmail’s coverage of Manchester United’s FA Cup clash with Middlesbrough.
Follow along for all the latest information including build-up, team selection and squad news. We will also be bringing you minute by minute coverage of the game.
Charlotte Daly
Host commentator