Wayne Rooney failed to convert a penalty as Manchester United lost 3-1 on spot-kicks 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 famous win.
United followed holders Chelsea and Arsenal in exiting the competition, while Middlesbrough set up a home quarterfinal with Everton.