Wayne Rooney failed to convert a spot-kick as Manchester United lost 3-1 on penalties to second-tier Middlesbrough in the League Cup on Wednesday.
After 120 goalless minutes at Old Trafford, the fourth-round tie went to penalties and with Rooney, Michael Carrick and Ashley Young all fluffing their lines, Championship side Middlesbrough pulled off a memorable win.
United followed holders Chelsea and Arsenal in exiting the competition, while Middlesbrough set up a home quarter-final with Everton.
“You can say it’s unlucky, but I said that after the City match also,” said United manager Louis van Gaal, whose side drew 0-0 with Manchester City on Sunday.
“You have to force the luck, but we didn’t do that because we didn’t score. That’s why I’m disappointed.”
A low-key game that saw Van Gaal make nine changes to his starting XI sprang to life mid-way through the second half, with home defender Daley Blind the central figure.
The Dutchman was involved in two huge scares for United — first hacking the ball into his own net, only for the goal to be ruled out for offside, and then dispatching a back-pass that stand-in goalkeeper Sergio Romero almost allowed to bobble in for what would have been a comical own goal.
As the game ticked into injury time there was a flurry of chances, with Jesse Lingard hitting the post for United and Romero saving from Grant Leadbitter and Stewart Downing at the other end.
United pair Anthony Martial and Marouane Fellaini each had penalty shouts rejected in extra time and went close with headers, and the home side were left to rue their missed opportunities.
Rooney’s opening penalty was brilliantly saved by Tomas Mejias and with Carrick blazing over the bar and Mejias also denying Young, spot-kicks from Leadbitter, Downing and Ben Gibson took Aitor Karanka’s men through.
“I’m very proud of my players,” said Karanka. “It was an amazing night for them.”