Anthony Elanga missed the crucial penalty as Middlesbrough won the penalty shootout 8-7 at Old Trafford and knocked Man United out of the FA Cup in the fourth round.
It seemed almost impossible to imagine after a first-half in which Jadon Sancho put United in front, Cristiano Ronaldo missed a penalty and the hosts created an incredible amount of chances in a dominant display.
They were made to pay for that wastefulness though, when Matt Crooks equalised in controversial circumstances after the break even though Duncan Watmore handled the ball in the build-up.
It remained 1-1 after 120 minutes and following 15 perfect penalties in the shootout, Elanga blazed his spot-kick over the bar to send United crashing out as they fell to an extraordinary cup upset.
The Red Devils have now become the second former Premier League champions to be knocked out by Skybet Championship sides after Arsenal were dumped out by Nottingham Forest in the last round. United’s title hopes now rests in the UEFA Champions League and they are billed to travel to Madrid to face Atletico Madrid on February 23 in the first leg of the competition. The Red Devils are 19 points behind Premier League leaders Manchester City and are effectively out of the running for the title. Man United last won a silverware in 2017 under Jose Mourinho and could now go five years without one again.