London: Wayne Rooney failed to convert a penalty as Manchester United lost 3-1 on spot-kicks to second-tier Middlesbrough in the League Cup yesterday, 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 famous win.
United followed holders Chelsea and Arsenal in exiting the competition, while Middlesbrough set up a home quarter-final with Everton.
A low-key game that saw United manager Louis 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 into the net.
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 substitute Anthony Martial had a penalty shout for handball rejected and went close with a header in extra time, and the home side were left to rue their missed opportunities.
United's first penalty was saved by Tomas Mejias and with Carrick blazing over the bar and Mejias also saving from Young, spot-kicks from Leadbitter, Downing and Ben Gibson took Aitor Karanka's men through.
Meanwhile, Liverpool's new manager Klopp tasted victory at the fourth attempt as his side edged 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.
City breeze through
"It's better than a draw," Klopp told Sky Sports at Anfield 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.
"We were dominant, we played football and had our moments. Everything is OK."
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 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.
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 goals by 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.