Manchester United had to settle for a 0-0 draw tonight against PSV Eindhoven in an uninspired performance.
The result leaves Louis van Gaal's side second in Champions League Group B, just one point clear of tonight's opponents ahead of the final matchday.
If PSV win their next game against CSKA and United fail to defeat group leaders Wolfsburg, then the Premier League side will miss out on the knockout stages.
United had 61 per cent of possession tonight but despite seven shots on target, they could not fashion a goal.
Juventus' Mario Mandzukic, right, is flanked by teammate Paul Pogba after scoring during tonight's match (AP Photo/Massimo Pinca)
Meanwhile, Manchester City, who were already through before this evening, lost 1-0 at Juventus in Group D.
A first half goal from Mario Mandzukic ultimately proved to be the difference, with the Croatian scoring in the 18th minute when he shrugged off a challenge from his marker to steer home a cross from close-range.
City are now second in their group, two points behind Juventus.
Tonight's results
Malmö FF 0-5 PSG
Shaktar Donetsk 3-4 Real Madrid
Man Utd 0-0 PSV Eindhoven
Juventus 1-0 Man City
CSKA 0 - 2 VfL Wolfsburg
FC Astana 2 - 2 Benfica
Atletico Madrid 2-0 Galatasaray
B M'gladbach 4-2 Sevilla
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