Liverpool face an uphill task to qualify for the knockout rounds of the Champions League after suffering a 2-0 defeat away to Red Star Belgrade.
Milan Pavkov scored both goals as the group's basement club picked up their first win of the competition to give themselves hope of continuing in Europe.
Liverpool still have Napoli and Paris Saint-Germain to play and must now do it the hard way to finish in the top two.
But Liverpool should have been in front in the 17th minute when the ball ran kindly for Daniel Sturridge inside the six-yard box, but the England international somehow managed to blaze over the bar when completely unmarked.