Manchester United suffered a shock FA Cup fourth round exit as Championship club Middlesbrough won 8-7 on penalties after a 1-1 draw at Old Trafford on Friday.
Ralf Rangnick’s side crashed out after Anthony Elanga blazed his spot-kick over the bar in a nerve-jangling shoot-out.
Swedish teenager Elanga was the only player from either team to miss in the shoot-out, leaving the forward holding his head in disbelief as Middlesbrough celebrated their stunning victory.
Jadon Sancho had put United ahead in the first half, but Matt Crooks grabbed a controversial equaliser after the interval to set the stage for Middlesbrough’s memorable upset.
Cristiano Ronaldo had missed a first half spot-kick for United, who have now lost seven of their last eight penalty shoot-outs, including last season’s Europa League final against Villarreal.
United are without a major trophy in five years and their hopes of ending that drought are dwindling given their Premier League struggles and a tricky Champions League last 16 tie against Atletico Madrid.
The FA Cup embarrassment is the latest hammer blow for United at the end of a painful week that saw their England forward Mason Greenwood arrested over the alleged rape and assault of a young woman.
England international Greenwood, who was released on bail on Wednesday, has been suspended from all football activities at United since his arrest.