Liverpool's hopes of qualifying for the Europa League knockout stages suffered a setback after they went down 1-0 to Anzhi Makhachkala in Moscow on Thursday.
The Russian side struck the evening's only goal in first-half stoppage time when Lacina Traore skilfully spun Sebastian Coates and lifted the ball over Brad Jones.
Liverpool pressed in search of an equaliser after the break but it never came, while Anzhi were guilty of spurning some good openings themselves.
The pre-match team news confirmed a first ever senior start for Conor Coady in midfield. The 19-year-old formed part of a youthful Liverpool side which consisted of four teenagers, with Jon Flanagan, Adam Morgan and Andre Wisdom also in Brendan Rodgers' XI.
They were joined by more experienced colleagues Joe Cole, Jamie Carragher and Stewart Downing as the Reds looked to take a giant step towards qualification from Group A.
A handful of Liverpool fans made the 1,600-mile journey from Merseyside to Moscow, while Anzhi made a marginally smaller trek across Russia to the capital for the game.