Liverpool succumbed to a 2-0 defeat away to Red Star Belgrade, threatening their qualification to the knockout stages of the Champions League.
Red Star 2-0 Liverpool
‣ 1-0 - Milan Pavkov 22'
‣ 2-0 - Milan Pavkov 29'
Liverpool had lost just one of their last 11 Champions League group stage games going into this tie, winning five and drawing five.
They were hoping to consolidate their position at the top of Group C, with Napoli and Paris Saint-Germain playing the other fixture of the night.
Jurgen Klopp made three changes to the side that drew away to Arsenal on Saturday as Joel Matip, Adam Lallana and Daniel Sturridge started in place of Joe Gomez, Fabinho and Roberto Firmino.
It was an electric atmosphere in Serbia as the Reds looked for an important victory in Group C that would put them within touching distance of the knockout stages.
The Rajko Mitić Stadium, the setting for Liverpool's Champions League group C fixture against Red Star Belgrade / Image: Getty Images via Liverpool FC
The Reds created the first chance of the night as Sadio Mane escaped down the left and middled for James Milner, who hooked his volley over the bar from the edge of the box.
Mohamed Salah's driven cross was deflected by Sturridge into Trent Alexander-Arnold's path, however the youngster was only able to fire over the crossbar.
Red Star could have taken the lead not long after as a corner dropped for Vujadin Savic, who spun and hooked a shot not far over the crossbar from close-range.
With the opening 20 minutes coming to an end, it was the visitors that had the best chance of the evening via Sturridge.
Mane ran into acres of space and crossed for Andy Robertson, who tried to sweep the ball into the corner, but it ended up in Sturridge's path, who scooped over from less than 5 yards out.
The striker was at the end of a swift Liverpool counter minutes after, but this time his shot was blocked and deflected behind.
Red Star then piled the pressure on as Nabouhane's first-time effort from range was met by Alisson.
The Serbs finally got their breakthrough from the ensuing corner as Milan Pavkov planted a firm header into the back of the net, evading Virgil van Dijk and past Alisson.
Red Star then doubled their lead as Pavkov picked up the ball and held off a challenge, unleashing a long-range shot from 25 yards out that evaded Alisson's reach.
Liverpool were rattled as the home crowd's noise intensified but they looked to get back in the game as Gini Wijnaldum and Lallana both came close but had shots blocked by a resilient Red Star defence.
The Reds entered the break 2-0 down and had plenty to do to get back into the game as Klopp introduced Gomez and Firmino in place of Alexander-Arnold and Sturridge.
LFC News - Red Star 2-0 Liverpool Highlights - Liverpool crash to a shock defeat in the Champions League on Tuesday night / Pic by David Rawcliffe/Propaganda
Liverpool had a much more encouraging start to the second half as they looked to half the deficit, but Red Star continued to look threatening with a range of long throw-ins.
Mane went close as he headed Firmino's deflected cross towards goal, but he failed to get enough power behind the ball, losing his footing in the process.
The Reds kept the ball far better than the first half, but failed to create any clear cut chances as Red Star's home support got behind their side.
Salah had two quick chances as he hit the outside of the post following a corner and then the Egyptian's deflected drive from the edge of box was pushed behind by Borjan.
With 12 minutes to go, Klopp replaced Lallana for Divock Origi, who made his first appearance of the season from the bench.
Liverpool continued to look for their opening goal, with Van Dijk and Matip causing problems for Red Star at Gomez's long throw. The ball fell for Salah once more, but he was unable to turn home in a congested box.
Firmino then stood up cross to the back post, but Van Dijk's header went over the crossbar and on to the roof of the net.
LFC News - Red Star 2-0 Liverpool Highlights - Liverpool crash to a shock defeat in the Champions League on Tuesday night. Pic by David Rawcliffe/Propaganda
Liverpool remain top of Group C with six points, although they are likely to be overtaken by either Napoli or PSG, who have five and four points respectively.
The Reds face an uphill task of qualifying for the knockout stages, with an away trip to PSG to come in the next round of fixtures, before they finish against Napoli at Anfield on match-day six.
Liverpool: Alisson, Alexander-Arnold, Matip, Van Dijk, Robertson, Wijnaldum, Milner, Lallana, Mane, Salah, Sturridge.
