This miserable night in Eindhoven offered Manchester United a humbling return to the UEFA Champions League.
The effects will stretch for as long as it takes for Luke Shaw to recover from the double right leg fracture suffered inside the opening 15 minutes, but they start with this 2-1 defeat to a competent and composed PSV Eindhoven side.
United appeared on course to overcome Shaw's gruesome injury and start this European campaign with a victory when Memphis Depay slotted home against his former side after 41 minutes. PSV rocked in the subsequent minutes before conjuring an equalizer through Héctor Moreno in first-half stoppage time. Luciano Narsingh finished a tidy sequence just before the hour to send United spiraling to defeat.
PSV earned the points with a determined, incisive response to falling behind, but United failed once again to translate possession into sharpness in the final third. The lack of menace eventually cost United dearly on the night and placed Louis van Gaal's side in a difficult position to start Group B play after VfL Wolfsburg's 1-0 victory over CSKA Moscow in Germany.
Optimism brimmed at the outset of United's return to this grand stage after a one-year absence. Anthony Martial took the central striking berth after his goal against Liverpool at the weekend, while Juan Mata operated as the creative fulcrum with Wayne Rooney ruled out with a hamstring complaint.
Most of the intent inevitably emerged from Depay on the left. The former PSV winger returned to the club he left in the summer and threatened from the outset. His cross from the left created a half-chance for Martial inside the opening 10 minutes as United searched for an opener.
Those efforts halted promptly after Shaw incurred a serious right leg injury at the end of slicing run toward the penalty area. Moreno claimed the ball with his last-ditch tackle, but he caught the England fullback as he finished it. Medical staffers attended to Shaw for 10 minutes before transporting him off the field and the injury surely had an affect on players in the first half.
"I didn't see it first hand but I know that a few of the players did witness it," Chris Smalling told reporters after the match. "It's a very sad time and we wish him a quick recovery."
United adjusted tactically by shifting Daley Blind to the left and summoning Marcus Rojo from the bench. It took both sides several minutes to process the sobering and unfortunate events, but United eventually mustered its reply with the opening goal after 41 minutes.
Blind stepped into space on the left and slotted a ball for Depay in behind Santiago Arias. Depay collected and immediately sliced into the channel. The resulting grace -- a couple of quick touches, a clever move to split two defenders -- paved the way for a precise finish inside the far post to provide United with a foothold.
The goal encouraged United and staggered PSV in the subsequent moments. Depay rounded off a storming counter by pushing his effort just wide of the far post. United captain Smalling caught Maxim Lestienne in possession and then forced Jeroen Zoet to parry.
Just as United appeared poised to wrest firm control, they conceded the equalizer. Smalling scuffed an initial clearance on a ball over the top and conceded a corner from Lestienne's resulting cross. Lestienne whipped his service toward the near post for the poorly marked Moreno to nod toward the far post. Blind attempted to head clear, but the ball skimmed off the top of his head and tucked into the net.
PSV's equalizer renewed the conviction and the intent of the home side after the break. The ambition and the energy of wingers Lestienne and Narsingh posed a recurring threat to United's recalibrated back four and eventually paved the way for the winner after 57 minutes.
Once again, United caused many of their own problems with carelessness in the back. Andres Guardado intercepted Matteo Darmian's ill-advised pass up the right and promptly sent Lestienne into the space behind him. United struggled to compensate after the initial error and watched as Narsingh glided free at the back post to head home the winner.
United searched earnestly for an equalizer in the final half-hour without mustering the sort of threat required. Mata squandered perhaps the best chance when he failed to control Bastian Schweinsteiger's ball over the top in the moments after the goal, but United struggled to produce opportunities of a similar quality in the waning moments. The final whistle left PSV to celebrate a 13th consecutive match without defeat and sent United off to wonder about the ramifications of this night in the short-term and for the remainder of this European campaign.
"We needed that cutting edge in the final third, in the box, to try to make more of our possession," Smalling told BT Sport 2 after the match. "But I think in the first half they scored from their only chance. They punished us with their main two chances so it's a very disappointing night."
He added: "We scored a good goal and then we couldn't really kick on from that and we've got a lot to learn to make sure we bounce back on Sunday."