Manchester United were forced to a 0-0 draw at Old Trafford by PSV Eindhoven that left the English side facing elimination from the UEFA Champions League.
The draw means United are yet to qualify for the last 16 of the Champions League when a victory would have seen them through.
United go to Wolfsburg for their final group match and a draw, combined with a PSV victory over already eliminated CSKA Moscow would end Louis van Gaal's men's hopes.
Bastian Schweinsteiger registered the first effort of the game, but his 25-yard shot was easily dealt with by Jeroen Zoet. A few minutes later, Memphis Depay forced his former teammate into a low save at his near post after cutting in from the left.
PSV were forced into an early change as Luciano Narsingh hobbled off to be replaced by Gaston Pereiro after just 18 minutes and the visitors struggled in the opening half an hour.
On his return to the side, Wayne Rooney squared a low cross to Jesse Lingard, but the youngster's first touch escaped him and Zoet gathered the loose ball.
Zoet was on hand again to deny Morgan Schneiderlin in the 31st minute, while David de Gea was called into action to clutch Jorrit Hendrix's curling strike from the air.
Anthony Martial then had two chances before half time, but Zoet was equal to both of the Frenchman's strikes.
Louis van Gaal's side came out firing in the second half and had three opportunities in the five minutes after half time. Schneiderlin and Lingard went close with headers before Depay fired in a low shot which was saved by Zoet.
Davy Propper fired a vicious volley at goal in the 62nd minute, but it was straight at De Gea, who saved comfortably.
The visitors then led a direct counter-attack six minutes later, but Jurgen Locadia dragged his effort wide when he had teammates in support.
Van Gaal threw on Marouane Fellaini, Ashley Young and Juan Mata as Man Utd searched for a second-half winner, but Lingard wasted the best opportunity of the game as he skied a shot over the bar from 12 yards after Young had cut the ball back to him.
The hosts were unable to create any more clear-cut openings in the final 15 minutes as PSV held on for a crucial point to keep them in the hunt for qualification from Group B.