Juventus, Paris Saint-Germain, Atletico Madrid and Benfica became the latest teams to qualify for the last 16 of the Champions League while Manchester United squandered a chance to join them on Wednesday.
Louis van Gaal's Manchester United were held to a 0-0 draw at home to PSV Eindhoven.
On a night when Old Trafford marked 10 years since the death of United legend George Best, the hosts saw plenty of the ball but created few genuine chances, with Jesse Lingard hoisting their clearest opportunity over the bar mid-way through the second period.
Coupled with Wolfsburg's 2-0 win at CSKA Moscow, the result saw United concede top spot in Group B and leaves them needing to win their final game at Wolfsburg on December 8 to be certain of a place in the knockout phase.
"The result is disappointing because I have still the feeling that we could have finished this game several times," said van Gaal.
"That's disappointing because we have to win in Wolfsburg and that's also a difficult game. We have to do it in Wolfsburg."
Phillip Cocu's PSV have now taken four points from United, having beaten them 2-1 in September, and will approach their final assignment at home to CSKA two points behind group leaders Wolfsburg and one below United in third place.
"It's a great opportunity," said Cocu, who played under van Gaal with Barcelona and the Netherlands.
"I'm happy with the result. It was a great team performance, but we're not there yet."
Last season's runners-up Juventus beat Manchester City 1-0 in Turin thanks to a Mario Mandzukic goal to join the English side in qualifying from Group D.
PSG romped to a 5-0 victory in Malmo, with Zlatan Ibrahimovic scoring against his boyhood club, as they confirmed their place in the knockout draw along with Real Madrid from Group A.
Atletico Madrid are through from Group C after a 2-0 victory at home to Galatasaray and that result ensured Benfica, who drew 2-2 at Astana earlier, also progressed.
In total, nine clubs have qualified for the last 16 with a game to spare as holders Barcelona and Bayern Munich went through on Tuesday and Zenit St Petersburg were already through.
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