It was a sorry night for Louis van Gaal in Holland as United made a losing return to the Champions League, with Luke Shaw's double leg fracture adding to Man United's woes.
Manchester United full-back Luke Shaw has emerged as one of the shining stars of their season to date and yet this was a night when his dreams were shattered in agonising fashion.
After a few weeks that has seen the 20-year-old beginning to realize his potential after a difficult first season at Old Trafford, Shaw was emerging as a potent attacking weapon on the left side of the United team that dominated the early exchanges of their opening Group B tie against PSV Eindhoven.
That before Shaw's burst of offensive ambition that resulted in his moment of agony after 15 minutes.
A desperate last gasp challenge from Hector Moreno as the England defender threatened to open the scoring and within seconds of Shaw hitting the turf, it was clear that he had sustained a serious injury, with the club confirming post-match it was a double fracture to his right leg and would be transferred to Manchester to be operated on.
The nine-minute stoppage that followed concluded with a rousing ovation for Shaw as he was carried from the field with an oxygen mask providing him with a modicum of relief in his moment of despair.
United’s sympathy for Shaw will quickly be replaced with a realization that his absence from their defensive line for a sustained period will now expose their lack of strength in depth in defensive positions.
Manchester United manager Louis van Gaal questioned whether his team were ready to make their mark in the Champions League ahead of kick-off in this game and in all but one area, they provided him with a positive answer.
Against the top seeds in Group B and playing away from home, United dominated possession from the off and they created more than enough chances to ensure that they left Holland with a share of the spoils at the very least, yet their lack of cutting edge came back to haunt them once again.
A superbly taken goal from Memphis Depay four minutes before the break handed United a platform to secure a victory that would have put them a giant stride towards the knock-out phase of the competition, with Depay, Anthony Martial, Chris Smalling and Juan Mata all missing glorious chances to add to their goal tally.
The possession statistics (62%-38% in United’s favour) confirmed that the visitors were the dominant side, with United keeper David De Gea a spectator in this game apart from his duty of picking the ball out of the net on two occasions.
Are United regretting their decision to allow Robin van Persie to leave for Galatasaray during the summer?
Should they have done more to sign a more experience striker to compliment the arrival of Anthony Martial?
On this evidence, the answer to both of those questions was in the affirmative and this area of weakness will continue to undermine United’s efforts until Van Gaal is given the striking options he needs.
United boss Van Gaal had little option other than to start with teenage striker Anthony Martial in Eindhoven, yet you sense it was a selection he would rather not have made.
With skipper Wayne Rooney out Marouane Fellaini feeling unwell ahead of the, Van Gaal hinted prior to kick-off that his selection of Martial was forced upon him, in a confession that said much about United’s lack of attacking options this season.
Van Gaal was not merely taking the weight of expectation away from Martial when he suggested that his successor as United boss would benefit from the club’s staggering decision to pay £36m to sign Martial on transfer deadline day, but his progression to his first team has been unexpectedly accelerated.
Showing moments of inspiration and the odd classy touch, Martial is clearly a young man oozing with potential. It remains to be seen whether he is ready to lead the United line alone just yet, but Van Gaal’s limited striking options will ensure he gets plenty of first team exposure in the coming weeks.
With so much possession and chances aplenty created, United should have won this game with something to spare and yet they were undone by two moment of sleepiness at the back.
As Van Gaal encouraged his side to play with a high defensive line, PSV took advantage with a swift breakaway to score their second goal and the raucous cheers that greeted the final whistle from the home fans confirmed that they could not believe their team had pulled off this remarkable victory.
In truth, United could not have done too much more to get a positive result on his return to Holland and in the end, fate worked against the Dutchman and his team against a fortunate PSV team.
Wolfsburg’s 1-0 win against CSKA Moscow means that United’s game against the Bundesliga side in the next round of Champions League matches is now vital.
Victory at Old Trafford and Van Gaal will believe his side are in control of their own destiny in the Group B and yet this result leaves them in a precarious position, after PSV were handed a three point start in the race for a last-16 finish.
On this evidence, United should have more than enough to get the win they need against PSV on home soil in late November and Van Gaal can only hope that the door to the last-16 of the Champions League will still be open to his side at that stage of this group.