Liverpool were left scratching their heads and licking their wounds after a last-gasp Lisandro Lopez goal denied them a much-needed victory in Lyon.
A late Ryan Babel wonder-strike seemed to have given the Reds a vital three points in Champions League Group E, before Lisandro gave the home side an undeserved draw in the last minute of normal time.
Rafael Benitez's side have only themselves to blame for not returning to Merseyside with three points after bossing this tie for long periods and missing plenty of good opportunities before Babel netted.
After a nervy start, Liverpool were very much in control from the 12th minute when half-fit striker Fernando Torres was presented with a free opportunity in the area from Emiliano Insua's deflected cross, which he directed straight at Lyon keeper Hugo Lloris.
From there on in, Liverpool missed further good chances, with Dirk Kuyt seeing his dipping effort tipped over by Lloris who was in fine form.
The chance of the match fell to surprise selection Andriy Voronin, who raced clear of a napping Lyon back four.
One-on-one with Lloris, the Ukrainian seemed certain to score, but timidly shot straight at the keeper's legs to signal the beginning of a miserable night for the long-haired blonde who was eventually hauled off by Benitez.
Though the second period was more even, it was Liverpool who again created the goalscoring opportunities as the home side struggled to work Reds goalkeeper Pepe Reina.
Lisandro did almost beat the Spaniard after latching on to a poor headed pass back from Sotirios Kyrgiakos, but the home side were unable to muster anything of note on their own.
Liverpool saw another gilt-edged chance go begging when Lucas Leiva saw his effort saved by Lloris, before Kuyt's bicycle kick rebound was cleared off the line.
But substitute Babel finally broke the deadlock in the 83rd minute, when he collected a cross-field ball from Yossi Benayoun.
Cutting inside at a distance of 25 yards, the Dutch winger blasted the ball past Lloris who was this time powerless to prevent his side from going behind.
Cruising and seemingly destined to begin their Great Escape, Liverpool were stunned in the 90th minute as Lisandro ushered Kyrgiakos out of the way following a flick-on from a hopeful long ball.
The Argentinian coolly stroked home past Reina and sealed the home side's passage to the knockout stage.
The Reds must now rely on Lyon to do them a favour when they take on Fiorentina in Italy, while taking maximum points themselves against Debrecen.