Aston Villa missed the chance to all but secure their place in the Champions League knockouts as they were beaten by Monaco at Stade Louis II.
Wilfried Singo got the game's only goal in the eighth minute, heading home from close range after Emiliano Martinez had initially done well to keep out Thilo Kehrer's effort.
Villa were not at their best, but did have chances to equalise, with Monaco goalkeeper Radoslaw Majecki twice denying the visitors before half-time.
First, Leon Bailey forced him into a decent stop after good work by Emiliano Buendia, who also teed up Ollie Watkins for an effort straight at Majecki.
Monaco also had a goal ruled out early in the second half when Maghnes Akliouche was flagged offside, but the hosts continued to look the most likely to score again, twice getting in behind the Villa defence only for last-ditch blocks to prevent them scoring.
The defeat means Unai Emery's side will likely need to beat Celtic at Villa Park next Wednesday to seal a top-eight place in the league phase of the competition.
Meanwhile, the win boosted Monaco's own automatic qualification hopes as they moved alongside Villa on 13 points.
This will feel like an opportunity missed for Aston Villa, who knew a win would all but send them into the knockout stage.
Monaco had won just one of their last eight games in all competitions, with three of their last five home games ending in defeat.
But Villa's away form has also been poor in recent months. They had lost six of their nine games on the road before Tuesday's fixture, although their last two results were a 1-0 win at Everton and a 2-2 draw at Arsenal.
Against Monaco they struggled to put together moves to open up the defence and not even the introduction of super sub Jhon Duran early in the second half was able to inspire them into any improvement.
Boss Emery became visibly frustrated with his side's passing in the latter stages of the game, as sloppy play led to Monaco breaking on the counter a couple of times.
The result was a setback, but nevertheless Villa are still in a strong position to progress to the next stage in what has been a hugely impressive debut season in the competition.