And on the evidence of this display when they were pushed all the way Rochdale, they face an uphill task to reach the quarter finals.
This competition has traditionally a time for youth to take centre stage and United could be forgiven for thinking a second goal inside a week for 17-year-old Greenwood had sealed victory.
But the League One strugglers upstaged their illustrious neighbours and Premier League giants with an even younger hero in Matheson.
But while he might not be able to buy a pint he was responsible for another sobering night for Ole Gunnar Solskjaer’s misfiring side given his was his equaliser which took the tie to the wire.
In front of the Stretford End, United calmly buried five out of five, Juan Mata, Andreas Pereira, Fred, Greenwood and Daniel James finding the net. Sergio Romero saved Rochdale’s third from Jimmy Keohane.
Greenwood had looked to have rescued a sloppy United performance with a second clinical finish after his strike against Astana last Wednesday, firing home a left foot shot from the right side of the area after 68 minutes.
But having seen an close range effort from Callum Camps cleared off the line on 52 minutes, Dale finally got the breakthrough their efforts deserved eight minutes later, Matheson arriving unmarked at the near post and smashing Oliver Rathbone’s lofted cross high into the United net.
The day after Ed Woodward stressed to shareholders that Solskjaer remained the favoured architect of the long term rebuilding job at Old Trafford was not a good day to lose to a team from League One.
And there was acknowledgement of that in the inclusion of Paul Pogba after three matches out with an ankle injury, Jesse Lingard and Aaron Wan Bissaka.
But in truth this was a stuttering performance from United and a tie they should have put to bed five times over in the first half.
Marcus Rojo and Pogba both had golden chances to settle nerves in the first half – the latter appearing to have watched a little too much of the Rugby World Cup during his time off with an ankle injury.
Three times the Frenchman skied efforts over – the worst of which a header after being picked out unmarked six yards out with a perfect delivery from Wan Bissaka.
The full back had earlier managed to keep United in the tie clearing off the line when keeping out Camps’s close range stab from six yards on 52 minutes.
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