Manchester United have suffered Champions League away defeats before and will do so again, but the 2-1 loss to PSV on Tuesday night will taste as bitter as almost any.
The horrific leg break suffered by Luke Shaw after Hector Moreno's reckless challenge cast a shadow over the evening long before United fell apart and began hurriedly chasing their tails. Maybe they should have known it was going to be one of those nights the second they saw the left-back lying on the turf in complete agony.
The impact of seeing a team-mate suffer an injury as gruesome as Shaw's cannot be underestimated. United's players were clearly shaken up by the sight of the England star's twisted leg, with many keeping their distance to save themselves from registering the full horror. It just so happened to be a guy who was beginning to find peak form again too.
The player closest to the incident, and the first to signal the gravity of the situation, was Memphis Depay – the man who has quickly become Shaw's best friend since arriving at the club in July. It was a running joke throughout United's summer tour of the USA that the two had become immediately inseparable, always chatting, laughing and joking.
Depay even acknowledged Shaw's part in his bedding-in process in Monday's pre-match press conference, explaining that the 20-year-old's Premier League experience has helped him in his early adaptation to his new surroundings.
"Of course [Anthony Martial and I] are both young so we can help each other and ask each other questions," said the Dutchman. "The same goes for Luke Shaw, he has played in the Premier League a lot more than me so I ask him a lot of questions."
It was fitting, then, that Depay should put United ahead as Shaw headed for the hospital. His magical feet had Santiago Arias and Jeffrey Bruma tangled in knots, then he calmly slotted beyond Jeroen Zoet to leave his former PSV fans with wry smiles.
But Moreno was to live up to his role as the ultimate pantomime villain, heading home via a Daley Blind deflection from a left-wing corner in first-half stoppage time. Maxime Lestienne then found space in behind Matteo Darmian for at least the fourth time in the match but finally delivered a killer ball. Luciano Narsingh met it with an unstoppable header and United's horror night was complete.
By this time United were already looking like they were running out of ideas. Martial had started up front but after initial bright moments faded out of the game, unable to provide the focal point his side needed to plunder territory at key times. Juan Mata flickered but rarely shone, while the pacy outlets of Depay and Ashley Young were rarely allowed to flourish.
Behind them, Bastian Schweinsteiger often slowed the game right down, which benefited PSV a lot more than his own side, while Ander Herrera only ever seemed to pick up the pace when sitting deep.
Yet the loss of Shaw exposed them most glaringly. When Narsingh headed home at the far post there was neither Marcos Rojo nor Blind anywhere near him. A left side of defence which has looked refreshingly solid for most of this season suddenly seemed to be full of beginners rather than international regulars after Shaw's exit.
Blind had no joy at all after switching to left-back, while Rojo seemed well off the pace in his first official game since Argentina's loss in the Copa America final over two months ago. Issues which have been swept under the carpet amid a reasonably successful start to the season are evident once more.
"Tonight we were well and truly punished," admitted skipper Chris Smalling after the match, and he couldn't have put it better. But it is not as though a performance like this hasn't been coming given United's lack of a cutting edge of late.
It's almost a case of one step forward, two back these days at Manchester United. David de Gea signs a new deal, but Wayne Rooney picks up a hamstring injury. Anthony Martial delivers a stunning debut clincher, yet days later another young star is ruled out for a period of some months. A win against Club Brugge, a loss to Swansea. A victory over Liverpool, defeat to PSV.
The initial shock of Shaw's injury will fade in time, but the gap left by his absence will linger. So too will United's deep flaws which were truly exposed on an ugly night for Van Gaal in Eindhoven.
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