Liverpool's chances of qualifying for the last 16 of the Europa League were considerably reduced in Russia after Zenit St. Petersburg secured a 2-0 win thanks to goals from Brazilian forward Hulk and midfielder Sergei Semak.
In what has become Liverpool's last chance of claiming some silverware, Luis Suarez was the main culprit as he failed to hit the target despite being presented with four opportunities to open the scoring before Hulk blasted home from 25 yards.
The Reds immediately found themselves on the back foot as Zenit, who were playing their first competitive fixture since December 10, had a great opportunity to take an early lead when Hulk found space inside the area but his shot produced a fine save from Pepe Reina.
In a lively first quarter of an hour, Liverpool could have taken the lead after a poor pass from Nicolas Lombaerts was latched on to by Suarez who raced clear and went round the keeper only for the defender to atone for his mistake and dispossess the striker.
Suarez was Liverpool's main threat but it was Reina who was much the busier. Fortunately for Brendan Rodgers even when the Spaniard was beaten by a mishit shot from Hulk the ball cannoned into the post and Liverpool remained on level terms.
Playing the lone striker role Suarez once again went close as Joe Allen's cross found Raheem Sterling and the young winger squared for Suarez to attempt an outrageous flick which beat Vyacheslav Malafeev but went agonisingly wide.
On a bobbly surface that made it difficult for passes to be strung together it was a brilliant run from Glen Johnson just after half-time that almost handed Liverpool the lead but his shot was smothered by Malafeev.
A scrappy period of play followed as both sides were guilty of giving the ball away but it was Suarez who once again went close just after the hour mark.
Liverpool managed to work the ball forward at pace as Downing played it straight into the path of the Uruguayan who looked to curl it home from the edge of the area but it slid agonisingly past he post.
Suarez's misses then proved costly after a sensational goal from Hulk. The Brazilian latched onto the ball 30 yards from goal then took one touch before firing an unstoppable left-foot shot right into the top corner.
Just a matter of minutes later it was 2-0 after a curling cross to the back post cannot be cut out by Martin Skrtel and Semak has the simple task of poking the ball past a helpless Reina.
Suarez did eventually get one shot on target but his free-kick was easily saved and Rodgers decided he needed to bring on some extra cover in midfield, in the form of Lucas Leiva, to make sure no further punishment was delivered.
Liverpool will now have to produce another of those sensational European nights at Anfield in order to turn this tie around as they look to salvage their disappointing season.