Ashley Young was sent off as Manchester United s Champions League qualification hopes were dented by a 2-1 Premier League defeat at Wolves on Tuesday.
United would have moved up to third in the table, ahead of Arsenal and Tottenham, with victory at Molineux but Nuno Espirito Santo s side came from behind to win thanks to a Chris Smalling own goal.
Scott McTominay s first Manchester United goal put his side ahead but Diogo Jota, who scored as Wolves knocked Ole Gunnar Solskjaer s men out of the FA Cup last month, levelled.
Young s dismissal, the 100th of Mike Dean s Premier League career, came for a foul on Jota and in the 77th minute Smalling bundled the ball into his own net to ensure United have now lost three of their last four matches in all competitions.
The Donck s claiming it
— Wolves (@Wolves)
United started rapidly and Jesse Lingard fired wide after just six seconds before Romelu Lukaku headed a brilliant Diogo Dalot cross straight at Rui Patricio.
They did lead in the 13th minute, however. Fred fed McTominay and the Scotland midfielder steadied himself before arrowing a skimming 25-yarder across Patricio and into the bottom-left corner.
It was Fred s first Premier League assist but Wolves equalised when the Brazilian lost possession, Raul Jimenez splitting the United defence with a clever throughball for Jota to finish well.
Leander Dendoncker fired over from six yards and Matt Doherty nodded Joao Moutinho s free-kick wide but Lukaku went close to restoring United s lead before half-time.
Patricio s excellent reflexes kept out McTominay s header in the 55th minute after Paul Pogba flicked on Lukaku s left-wing cross.
Referee Dean then reached his milestone by sending off Young, the United captain shown a second yellow card after catching Jota with a high challenge.
And although Wolves had failed to record an effort on the United goal since the interval, Moutinho s sensational cross caused chaos in David de Gea s box and Smalling nudged the ball home, the United goalkeeper s flimsy challenge not helping.
De Gea prevented Smalling scoring a second own goal and Wolves almost extended their lead in added time, substitute Ivan Cavaleiro holding off Victor Lindelof but rattling the woodwork.
What does it mean? Top-four race tightens up
Tottenham s lack of form has blown the race for Champions League qualification wide open, but United are failing to take advantage and losing momentum at a crucial point of the season.
There are only three points between Arsenal in third and Chelsea three places lower, with plenty of twists and turns to come in the run-in.
Jota giving Wolves reason to dream
For the second time in recent weeks, Jota was a thorn in United s side. He took his goal superbly and could have won a penalty when Dalot clumsily halted an excellent run into the box.
If Wolves are to cap a stunning season by lifting the FA Cup, he will need to be at his best. Jota has now scored six goals in seven Premier League games at Molineux, providing a further three assists in that run.
9 Diogo Jota has had a hand in nine goals in his last seven Premier League games at Molineux (6 goals, 3 assists), having failed to score or assist a single goal in his first six at the ground. Turnaround.
— OptaJoe (@OptaJoe)
Young becomes Dean s landmark victim
Right-back Young, playing behind the impressive Dalot, had already been booked for an ill-timed tackle on Jota when he fouled the same player again five minutes later.
Dean may have a reputation for making himself the centre of attention but on this occasion the referee was given little option but to produce his red card. Young s dismissal contributed heavily to his side s defeat.
Key Opta facts
Wolves have won more points against ‘big six’ sides in the Premier League this season than any of the ‘other’ 14 teams in the competition (13 – W3 D4 L3).
Man Utd failed to win home or away against a promoted side in a single Premier League campaign for the first time since 2002-03 vs Man City.
Manchester United have lost consecutive away games against Wolves in all competitions for the first time since August 1980.
Following Ashley Young s dismissal, Mike Dean has now handed out 100 red cards in the Premier League, the most by a referee in the competition s history. Both of Young’s red cards in the competition have been shown by Mike Dean (also Jan 2009 for Aston Villa vs Sunderland).
Manchester United have had more different goalscorers (exc. own-goals) than any other Premier League team this season (16).
Raúl Jiménez has been directly involved in 19 Premier League goals this season (12 goals, 7 assists) – five more than any Wolves player has registered in a single season in the competition.
What s next?
Wolves go to Wembley on Sunday for an FA Cup semi-final against Watford. United have the weekend off before their Champions League quarter-final against Barcelona, the first leg set for Wednesday at Old Trafford.
