Red Star Belgrade secured their first-ever Champions League group stage win on Tuesday.
This was after two goals from towering striker Milan Pavkov helped the Serbian side to a memorable 2-0 home victory over a subdued Liverpool in Group C.
The 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.
Second-placed Napoli (five points) are at home to third-placed Paris St Germain (four points) later on Tuesday, with Liverpool facing both teams in the final two rounds.
Red Star, who are playing in the competition’s present format for the first time since they won the European Cup in 1991, also have four points after a spirited performance.
Pavkov, a surprise starter up front, gave Red Star a 22nd-minute lead when he headed home from the edge of the six-yard box after a Marko Marin corner from the right. It was no more than Red Star deserved after the opening 20 minutes.
Comoros forward El Fardou Ben Nabouhane forced Liverpool keeper Alisson Becker to palm his low drive from 25 metres around the post.
Alisson could do nothing, however, as 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 meters into the right corner of the net with Alisson well beaten. Liverpool, whose midfield struggled against their more aggressive opponents, lost possession on the halfway line and Pavkov shrugged off Georginio Wijnaldum to find the time and space to unleash an unstoppable shot.
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.
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.