Manchester - English champions Manchester United suffered a shock 2-1 defeat to Championship side Crystal Palace thanks to an extra-time goal from substitute Glenn Murray in their League Cup quarter-final on Wednesday.
Palace had not won, or even scored a goal, in five matches but took a surprise lead at Old Trafford with Darren Ambrose’s fine long-range strike.
Federico Macheda pulled one back from the penalty spot with his first goal at Old Trafford in 18 months.
But after the game went to extra time, Murray headed in to send the south London side into the semi-finals.
After the 6-1 defeat to City in October, it was just United’s second defeat at Old Trafford since their 2-1 loss to Chelsea in April 2010.
Crystal Palace manager Dougie Freedman said that it was a moment to treasure for a club that has had a hard few years.
"It's a wonderful night for the club, especially given the position we've been in the last few years," said Freedman, who as a player scored 95 goals in 330 appearances for the club.
"To play at Old Trafford tonight, we're privileged, the lads learnt a lot from tonight.
"I think we deserved it. We played some good stuff, some good football," added the former Scotland international.
Even though Sir Alex Ferguson made a host of changes to his team, United were still expected to take a place alongside Manchester City, Liverpool and another Championship side Cardiff in the last four.
But despite their recent problems, Palace started the game showing far more threat than the Premier League champions.
Wilfried Zaha looked a constant threat and the Palace winger fired just past the near post after a quick breakaway after just one minute.
The hosts finally went close when a sweeping move involving Antonio Valencia and Park Ji-Sung ended with Darron Gibson having a drive deflected wide. Dimitar Berbatov met the Gibson corner that followed but headed straight at goalkeeper Lewis Price.
Fabio had already been replaced by Ezekiel Fryers in the opening period and Berbatov, who seemed to have sustained an ankle injury in the first half, came off for Ravel Morrison at the interval.
Just after the restart, Republic of Ireland midfielder Gibson, who was making his first appearance of the season after a shoulder injury, drove wide from just inside the area.
And United should have opened the scoring when Anthony Gardner’s error let in Valencia but the winger’s cross-shot flew just wide of the post.
Morrison, making just his third appearance for United, also produced a powerful effort from around 25 yards that was held by Price.
Macheda also thumped an effort wide of goal after turning his defender on the edge of the area.
United’s injury problems continued when the other Da Silva twin, Rafael, limped off to be replaced by Paul Pogba just after the hour.
But in the 65th minute, Ambrose picked the ball up just inside the United half and found the top corner from 25 yards for his fifth goal of the season.
French youngster Pogba came close to a quick equaliser when he drilled a shot wide from just outside the area.
They got the chance to pull level when Patrick McCarthy pulled Macheda over in the area and the Italian got up to put the penalty in the bottom corner of the net.
After the game slipped into extra time, Gibson went close to breaking the deadlock with a powerful shot from 20 yards.
But seven minutes into the added period, Ambrose’s whipped free kick was glanced into the net by Murray.
After Macheda prodded a shot wide, Ambrose almost added a third with a swerving free kick from 35 yards that Ben Amos could only gather at the second attempt.
In the second period of added time, Palace were forced deeper and deeper but held on for their first win at Old Trafford since 1989.
Draw for English League Cup semi-finals played over two legs made on Wednesday:
Manchester City v Liverpool
Crystal Palace v Cardiff
Matches to be played weeks beginning January 9 and 23