A young Liverpool side slumped to a 1-0 loss to Anzhi Makhachkala in their Europa League Group A match at Moscow's Lokomotiv Stadium.
Lacina Traore made the difference during a turgid match in the Russian capital when he flicked the ball away from Sebastian Coates before planting a lob over Brad Jones and into the visiting net in stoppage time in the first period.
Steven Gerrard, Luis Suarez, Joe Allen, Nuri Sahin, Daniel Agger, Jose Reina, Glen Johnson Raheem Sterling and Jose Enrique did not travel ahead of the Reds's trip to play Chelsea in the Premier League at Stamford Bridge on Sunday.
Youngsters Stephen Sama, Adam Morgan and Conor Coady were called into the squad with Morgan and Coady starting the match in a team with an average age of under 24.
19-year-old Coady was among seven changes from the team that overcame Anzhi at Anfield a fortnight ago. 18-year-old striker Morgan made only his second start for the English side.
Liverpool passed the ball well, but could not find any finish to their openings. They slip to second in the section with this loss - their first defeat in the group stages of this tournament - as Anzhi move a point ahead of Brendan Rodgers's side with seven points from their four games.
Liverpool are second in the group ahead of Young Boys on goal difference after the Swiss side completed a 3-2 win at Udinese, who are bottom of the section with four points. Liverpool host Young Boys on November 22 before visiting Udinese on December 6. They may have to win those two games to progress in the tournament.
Not that it will bring Rodgers out in a cold sweat with worry as the side he stuck out in Russia means the Premier League clearly takes precedence over what he is trying to achieve in the Europa League.
Anzhi play 1,000 miles away from their home in Dagestan due to security issues. This was a fifth straight "home" win for Guus Hiddink's men in the competition.
There was not really much to write home about in the first period apart from Traore's goal, but Jones showed his ability with a fine diving leap to his left to prevent a Samuel Eto'o effort from finding the net midway through the half.
Jones was again equal to the task on 56 minutes as he held a curling Eto'o shot that was heading into the corner of the net.
Traoe had the chance to kill off the match when he headed straight at Jones on 72 minutes before slipping a shot wide from the edge of the opposition area when it looked easier to score.
Joe Cole could have brought Liverpool level when home goalkeeper Georgi Gabulov failed to hold a long-range effort from Suso, but it summed up Liverpool's struggles on the night when he knocked the ball straight at Gabulov before being replaced by Oussama Assaidi seconds later.