Red Star Belgrade 2 Liverpool 0
A damaging 2-0 defeat to Red Star Belgrade in Serbia sealed Liverpool's worst away run in Europe's elite club competition in 39 years and made qualifying from Group C that bit harder.
Two first-half strikes from Milan Pavkov, a 24-year-old scoring his first European goals in only his 11th appearance, were enough to beat the off-colour Reds.
A third successive Champions League away defeat, taking into account May's semi-final reverse in Rome, equalled the run of 1979 which was 'achieved' over three seasons, not three successive matches.
It posed plenty of questions for manager Jurgen Klopp, whose decision to leave Xherdan Shaqiri, of Kosovar-Albanian parentage, at home in order to lessen local hostilities, had no bearing on this performance.
There was an ominous feeling to Liverpool's 200th match in the Champions League/European Cup when, in the 17th minute, Daniel Sturridge missed a sitter.
Sadio Mane found space down the left to drill a low cross which evaded Mohamed Salah but found his team-mate at the far post, only for the striker to lean back and balloon over.
When Sturridge's right-footed shot on the turn deflected for a corner, the tide turned as the hosts turned the screw.
Goalkeeper Alisson Becker was forced to save low to his left after El Fardou Ben Nabouhane's shot from distance, but, from former Chelsea midfielder Marko Marin's resulting corner, Pavkov headed home.
Liverpool had the briefest of openings, but, uncharacteristically, Adam Lallana's first touch let him down as he tried to control Salah's square pass inside the penalty area.
The visitors were punished with exacting precision on the half-hour as James Milner gave away possession with a loose pass infield and the ball was quickly transferred to Pavkov, who smashed home his second from 25 yards.
It was only the third time this season they have conceded more than one goal, but the second occasion in the Champions League and the first time since October 2014 they had conceded more than once in the first half of a Champions League game.
Changes were needed and Klopp acted swiftly, bringing on Roberto Firmino and Joe Gomez at half-time for Sturridge and Trent Alexander-Arnold.
Within three minutes the Brazilian substitute had made his presence felt, cutting back only for Mane to make a half-hearted stab with the outside of his right foot from six yards.
Left-back Andy Robertson, playing almost as an out-and-out winger after the break, saw a cross deflected on to the top of the crossbar, while Salah finally forced a save out of Milan Borjan, hitting a post with his next effort.
The appearance off the bench from Divock Origi for his first minutes for the club since August 2017 highlighted how desperate the situation was.
Salah almost sneaked a close-range shot in between goalkeeper and post and Virgil van Dijk headed on to the roof of the net, but there never appeared to be any real threat of them recovering the deficit.