Manchester United crashed out of this season’s FA Cup as Championship side Middlesbrough won 8-7 on penalties after 120 minutes of football ended 1-1 at Old Trafford on Friday.
Young striker Anthony Elanga blazed his shot over the bar to send Middlesbrough into the next round.
It was only the second time in 11 meetings with Premier League opposition that Middlesbrough had progressed, following on from their equally surprising success at Manchester City in 2015.
Jadon Sancho seemed to have put United on the road to the fifth round when he marked his FA Cup debut with a goal.
United will complain about Middlesbrough’s controversial equaliser, scored by Matt Crooks, who tapped home despite Duncan Watmore clearly handling in the build-up.
The Red Devils would have themselves to blame after failing to take numerous chances in a game where they had 30 shots at goal, the clearest of which came when Cristiano Ronaldo missed a penalty in the first half.
The shocking defeat means United’s most realistic chance of silverware has now disappeared.
Meanwhile, the draw for the FA Cup fifth round will take place on Sunday.