Manchester United hoped to get revenge on PSV after their opening game group loss - but their effort at Old Trafford proved to be a damp squib.
The Red Devils were frustrated as they dawdled their way to a 0-0 draw, never really looking like scoring.
It leaves Louis van Gaal's side needing a win away to Wolfsburg to qualify - and the German side have not lost at home in the last 29 games in all competitions.
Former Liverpool defender Jamie Carragher said on Twitter that the Dutch side deserved credit for getting a point, and their performance merited it.
Man Utd will be disappointed they haven't qualified tonight but PSV were very good, excellent defensively & very good counter attack.— Jamie Carragher (@Carra23) November 25, 2015
Michael Owen was less diplomatic, taking United to task and calling out Louis van Gaal's tactics. He told BT Sport that United are set up too defensively and do not add enough in attack.
In last night's Champions League matches alone, 20 more players had more successful final third passes than Memphis Depay, who made the most of any United player with 16.
These included five Manchester City players in their match with Juventus, with both full-backs Bacary Sagna and Gael Clichy among them.
Atletico Madrid's Koke made the most final third passes of any player last night with 63.