Wolves 2-1 Man United
Manchester United endured another nightmare trip to Wolves as Ole Gunnar Solskjaer's men slumped to their third defeat in four matches.
It came just 17 days after the Norwegian, then caretaker manager, bemoaned the "poorest performance" of his reign, with Nuno Espirito Santo's side deservedly reaching the FA Cup semi-finals at United's expense.
The visitors started their Molineux return well but wasted a number of chances either side of Scott McTominay's superb first goal for the club, allowing Diogo Jota to level before Ashley Young became the recipient of Mike Dean's 100th Premier League red card.
Chris Smalling's own goal sealed Wolves' 2-1 comeback win, sending them to Wembley in high spirits as Solskjaer's men not only blew the chance to exact revenge but also to reassert themselves in the top-four race.
United should have been three up midway through the first half, with Romelu Lukaku - in for the injured Marcus Rashford - and Jesse Lingard wasting glorious opportunities in between a fine McTominay strike.
Fred's heavy touch from a David de Gea pass was ruthlessly punished as Jota was put behind to level, before being clattered by Young in the 57th minute as referee Dean showed the United captain a second yellow card.
From there it was always going to be an uphill battle, with Smalling turning into his own goal as Solskjaer tasted defeat as permanent United boss for the first time.
Wolves, by contrast, head to Wembley for Sunday's FA Cup semi-final clash against Watford in high spirits.
Wolves' goalscorer Jota said: "It's one more win and it's not important for us if it's against United or not. It's three more points for us and we are happy.
"We played against them two or three weeks ago and they started this game very intensely. We conceded a goal. We made a comeback and we are happy."
Striker Raul Jimenez added: "We know in these type of matches we have to do more than 100 per cent. We keep looking forward to winning this kind of game and that's what we want."
Lingard had an attempt within seconds of kick-off and Lukaku should have done better than heading at Rui Patricio following fine work by Diogo Dalot.
United had as many shots on target in the opening five minutes as they managed over 90 minutes of last month's FA Cup quarter-final - a bright start that led to a 13th-minute opener.
Fed by Fred around 25 yards from goal, McTominay rolled the ball and unleashed a low, fizzing effort that beat Patricio to the goalkeeper's right.
It was a superb way for the Scotland international to open his United account and Lingard should have added to it within four minutes when found unmarked from a Lukaku pass.
United could have been 3-0 up but Wolves were jolted into life midway through the first half.
Jimenez's strike over from an acute angle was swiftly followed by the previously impressive Fred meeting a De Gea pass with a heavy touch.
Wily Wolves midfielder Joao Moutinho reacted quickest and broke, with Jimenez delicately putting Jota in behind to turn home a 25th-minute equaliser.
Leander Dendoncker, Matt Doherty and Ruben Neves had attempts as United wobbled.
Lukaku struck just across the face of goal before the break, which United returned from looking to have settled down.
Fred tried his luck before McTominay got on the end of a deflected shot, only to be denied by a strong hand by Patricio.
Young was booked just before that effort and was soon off in the 57th minute.
The United captain's late challenge on Jota led referee Dean to dish out a second yellow card.
United were on the backfoot as Wolves unleashed wave upon wave of attack, with penalty claims after Jota went down under pressure from Dalot ignored.
Solskjaer's side were managing half chances but their defence was looking unsteady, with that instability leading to a 77th-minute goal when a cross from the left was not dealt with as Phil Jones challenged Jimenez, with Smalling inadvertently prodding into his own goal.
De Gea prevented another Smalling own goal, before Ivan Cavaleiro then rattled the crossbar as a bad night threatened to get even worse for United.
WOLVERHAMPTON WANDERERS: Patricio, Bennett, Coady, Boly, Doherty, Dendoncker, Neves (Saiss, 84 mins), Moutinho, Vinagre (Jonny, 76 mins), Jimenez, Jota (Cavaleiro, 73 mins).
Subs not used: Costa, Gibbs-White, Ruddy, Traore.
ManCHESTER UNItEd: De Gea, Young, Smalling, Lindelof, Dalot (Pereira, 84 mins), McTominay, Fred (Jones, 65 mins), Pogba, Shaw, Lingard, Lukaku (Martial, 73 mins).
Subs not used: Mata, Rojo, Romero, Matic.
Man of the match: Jimenez
Match rating: 7/10
Referee: Mike Dean