Both Manchester football clubs have been let leads slip to lose 2-1 in their Champions League group stage openers.
Luciano Narsingh scored a second-half winner as Dutch club PSV Eindhoven came from a goal down to beat visiting United 2-1 on a night of setbacks for the English side in the Champions League.
United's England left back Luke Shaw suffered a double leg break and was taken off on a stretcher with an oxygen mask strapped to his face in the early stages of the Group B game, which added to the eight minutes of injury time at the break.
Once play resumed, United's Memphis Depay returned to the club where he made his name and reminded spectators at the Philips Stadium of his prowess with a stunning 41st-minute opener.
PSV, however, caught the visitors napping at a corner in first-half stoppage time as Hector Moreno equalised before a swift break away set up the 57th-minute winner.
Juventus came from behind to hand Manchester City their first defeat this season as Mario Mandzukic and Alvaro Morata gave the Italian champions an opening 2-1 win in Group D in Manchester.
Premier League leaders City were fortunate to go ahead after 57 minutes when Vincent Kompany, climbing all over Giorgio Chiellini, saw the defender head an own goal as the home skipper wheeled away to celebrate instead of being punished for a foul.
But Juve pulled level in the 70th minute when Mandzukic touched the ball in off the post after Paul Pogba sent in a high cross from the left.
It was the first goal City had conceded after five domestic league wins so far this term but worse followed when Morata scored with a 20-metre left-foot curler in the 81st minute to snatch all three points.
In other feature games, Real Madrid beat Shakhtar Donetsk 4-0 and Paris St Germain beat Malmo 2-0.