Championship outfit Middlesbrough have knocked Manchester United out of the League Cup, winning 3-1 on penalties after drawing the match 0-0 following extra time.
Both sides struggled to create chances in the first half, and United's first attempt came after 30 minutes when Jesse Lingard saw a powerful effort blocked by Daniel Ayala, before James Wilson fired a tame effort towards Boro keeper Tomas Meijas.
Boro almost took the lead before the break, as Sergio Romero kept out a chipped effort by striker Kike, before the Argentina international tipped a Stewart Downing effort from 25 yards over the bar.
United came close to finding the opener after the break, as Andreas Pereira won possession before finding Memphis Depay, who forced a low save from Meijas with a powerful drive.
The visitors thought they had taken the lead on the hour mark, as Kike hit the post before the rebound hit Daley Blind on the way to the United goal, but the linesman had flagged for offside against the Spanish striker.
Substitute Ashley Young twice came close to setting up a goal before the final whistle, as Marouane Fellaini headed straight at Meijas from a cross, before Chris Smalling headed wide of goal from a corner.
The game came alive in added time, as Lingard forced a save from Meijas with a powerful effort before Romero denied both Grant Leadbitter and Downing.
Chances were at a premium in extra time, as George Friend fired wide from 30 yards in the first period, before Pereira did similar from the outside of the Middlesbrough box after the break.
United came close to snatching a win before the penalty shootout, as Fellaini twice missed the target from aerial opportunities either side of a close-range chance for Anthony Martial, who headed over the bar.
After Leadbitter had scored Boro's first penalty, Wayne Rooney was denied by Meijas, but the visitors could not take advantage as David Nugent fired over the bar.
Pereira and Downing successfully converted their spot kick attempts, before Michael Carrick gave Boro the advantage by firing high and wide.
Young defender Ben Gibson converted Boro's fourth penalty, before Meijas stopped Young's attempt to send the Teeside outfit to the quarter-finals, where they will play Everton at the Riverside Stadium.
