Capital One Cup
Round of 16
Full Time: Manchester United 0-0 Middlesbrough(Middlesbrough progress 3-1 on penalties)
Date: 28 October 2015
Venue: Old Trafford
Middlesbrough dumped Manchester United out of the English Capital One Cup, winning 3-1 in a penalty shoot-out after 120 minutes at Old Trafford finished goalless on Wednesday night.
It was not the most entertaining first half with neither side really able to impose themselves in attack.
Instead, both teams squandered possession in the final third with some poor passing and bad decision making.
Consequently, chances on goal were at a minimum.
Middlesbrough's only real opening came in the 16th minute after a goalmouth scramble inside the United box following a corner-kick, but George Friend failed to make the most of it after firing the ball straight at the keeper from close range.
The Red Devils only had one significant attempt on goal, and in fact it was their first shot on goal, in the 34th minute when a 16-yard effort from James Wilson was well-saved by the keeper.
The half ended goalless.
The start of the second stanza saw the introduction of striker Wayne Rooney for the home team and that made a positive impact as the game opened up a bit.
In the 54th minute some good work in the midfield from Rooney saw him win the ball and play Memphis Depay into space, but his long range shot was well-saved by the keeper.
Ten minutes later United nearly conceded in the most bizarre fashion when a back pass from Daley Blind was almost let into his own goal by Romero after the ball slipped under his foot, but the goalkeeper recovered to clear.
The play swung from end to end after that as both side's showed no fear in pushing numbers forward, but neither could find the back of net.
United came closest in the dying minutes of regular time when a 14-yard shot from Jesse Lingard struck the crossbar.
Regular time ended 0-0 and the game moved into an additional 30 minutes.
Both teams tired in extra time and neither could find a winner as the game ended goalless after 120 minutes and moved into the dreaded penalty shoot-out.
Three missed penalties from Wayne Rooney, Michael Carrick and Ashley Young saw Middlesbrough run out 3-1 winners in the shootout.