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, while Jurgen Klopp’s Liverpool edged Bournemouth.
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.”
Liverpool’s new manager Klopp tasted victory at the fourth attempt as his side beat Bournemouth 1-0 at Anfield.
Liverpool had recorded draws against Tottenham Hotspur, Rubin Kazan and Southampton in Klopp’s first three games after succeeding Brendan Rodgers, but Nathaniel Clyne’s first-half strike got the German off the mark.
“It’s better than a draw,” Klopp told Sky Sports with a wry smile.
“I’m really satisfied tonight because this team never played together since I’m here — young players, new players, players who didn’t play for a long time because of injuries — and they did really well.”
Clyne struck in the 17th minute, following up after Joao Teixeira’s audacious back-heel had been cleared off the line to score his first Liverpool goal and set up a quarter-final at his former club Southampton.
Premier League leaders Manchester City will host Hull City in the last eight after a routine 5-1 home victory over Crystal Palace, which came at the cost of an injury to right-back Pablo Zabaleta.
Wilfried Bony headed City in front from Aleksandar Kolarov’s 22nd-minute corner before Kelechi Iheanacho teed up Kevin De Bruyne to tap in his sixth goal in nine club games shortly before half-time.
Zabaleta was stretchered off early in the second half after hurting his knee in a collision with Wilfried Zaha, with Bacary Sagna replacing him.
City manager Manuel Pellegrini said the Argentine had damaged the medial ligament in his right knee and would undergo tests on Thursday.
Second-half goals by Iheanacho, Yaya Toure, from the penalty spot, and 17-year-old substitute Manu Garcia sealed victory, with Palace replying through Damien Delaney’s 89th-minute header.
Meanwhile, Aston Villa began life without sacked manager Tim Sherwood by losing 2-1 at Premier League rivals Southampton, who won courtesy of second-half goals from Maya Yoshida and Graziano Pelle.
Tuesday’s results opened up the competition, with holders Chelsea losing 5-4 on penalties at Stoke City after a 1-1 draw and a second-string Arsenal team crashing 3-0 at second-tier Sheffield Wednesday.
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