Manchester United squandered a lead to lose 2-1 at PSV Eindhoven and had left back Luke Shaw carried off with a broken right leg on an unhappy return to the Champions League on Tuesday.
Shaw required oxygen while he was taken off on a stretcher after being hurt by a two-footed tackle from Hector Moreno tackle in PSV's area in the 15th minute. Images showed Shaw's right foot was bent at a 45-degree angle and United said after the match that Shaw "suffered a double fracture of the leg."
"It is awful," United manager Louis van Gaal said. "When he came into the dressing room, he had an oxygen mask and was crying."
Memphis Depay, signed from PSV this summer, gave United the lead in the 41st minute of the Group B match by dribbling between two defenders and shooting through the goalkeeper's legs.
Moreno equalized in the lengthy period of first-half stoppage time — caused by his challenge on Shaw — with a header that deflected in off United defender Daley Blind. Luciano Narsingh's 57th-minute goal secured victory for the Dutch champions, who were the top seeds in the group but arguably the weakest team out of United, Wolfsburg and CSKA Moscow.
For United, the disappointing result of its first Champions League match in 17 months will be overshadowed by the injury to Shaw, whose displays this season demonstrated why the club made him one of the world's most expensive teenagers by signing the then-18-year-old in the summer of 2014 for $46 million.
"Defeat hurts," United goalkeeper David de Gea said, "but Luke Shaw's injury hurts even more."
Shaw was running into the PSV penalty area when he was felled by a challenge from Moreno. He was clearly in pain as he fell to the ground and there was a delay of about eight minutes as medical staff attended to him on the pitch.
Not even a foul was awarded and United would have felt a sense of injustice when Moreno rose in the second minute of stoppage time to head in a ball that flicked off Blind and into the net.
"When I say it's a penalty and a red card, I'm a bad loser," Van Gaal said of Moreno's tackle on Shaw. "It was a bad tackle with two legs."
A brilliant piece of skill from Depay earned United the lead. The Dutch winger cut inside from the left, weaved between two tacklers and finished low with his left foot. Depay has been saving his best displays for United for the Champions League, scoring twice against Bruges in the qualifying playoff.
Shaw was replaced by Marcos Rojo and the Argentina international's slack defending led to PSV's winner. A floated cross from the left by Maxime Lestienne went over the head of Rojo and was met by Narsinghe, who nodded in.
Juan Mata wasted United's best chance at an equalizer, miscontroling with the goal gaping after being found by Bastian Schweinsteiger.
"We can only blame ourselves because we have created so many chances," Van Gaal said. "You have to be effective and PSV were very effective because they scored out of nothing. A deviated ball from a corner kick and another finish after a passing error in the first phase."
Wolfsburg beat CSKA Moscow 1-0 in the other Group B match.