Red Star Belgrade secured their first-ever Champions League group stage win after two goals from towering striker Milan Pavkov helped the Serbian side to a memorable 2-0 home victory over Liverpool in Group C.
Tuesday's result left Liverpool on six points from four games and facing a tricky path to the knockout stages after the setback in the cauldron of Red Star's Rajko Mitic stadium.
Giant killers: Red Star players wave to their fans after full time.Credit:AP
Pavkov scored in the 22nd and 29th minutes and it was then left up to Socceroos defender Milos Degenek and his able defence to keep the Reds out.
Liverpool face Napoli at home and Paris St Germain away in the final two rounds and find themselves in a tricky situation.
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Red Star, who are playing in the competition's present format for the first time since they won the European Cup in 1991, put in a spirited performance.
Pavkov gave Red Star the lead when he headed home from the edge of the six-yard box after a Marko Marin corner from the right.
Alisson could do nothing when Marin swung in the corner and Pavkov rose above his markers to spark wild celebrations among the fervent 55,000 home crowd.
The atmosphere reached fever pitch seven minutes later as Pavkov doubled the home side's advantage, rifling a screaming shot from 25 metres into the right corner of the net with Alisson well beaten.
Mohamed Salah fired over the bar shortly afterwards to sum up a poor first half for Liverpool, with Daniel Sturridge also missing an early chance for the visitors when he volleyed over the bar from close range.
Salah missed two good chances within a minute for Liverpool midway through the second half, forcing a good save from Red Star keeper Milan Borjan before he shaved the outside of the post with a shot from the edge of the penalty box.
Drawing a blank: The usually prolific Mo Salah.Credit:AP
The outstanding Borjan again denied Salah from close range in the 82nd minute as Liverpool piled on the pressure but the visitors could not find a way through Red Star's packed and well-organised defence in which Degenek played a major part.
In France, home team Monaco were handed a humiliating defeat that all but ended the club's Champions League campaign as Thierry Henry once again failed to secure a maiden win as coach.
Monaco, semi-finalists in 2017, slumped to a 4-0 home loss to Club Brugge, who registered their first win in four Group A matches.
Hans Vanaken scored twice for the Belgian team, Brazilian forward Wesley made it 3-0 and captain Ruud Vormer completed the rout.
Reuters
