Liverpool face an uphill task after losing 2-0 to Zenit St Petersburg in the first leg of their Europa League last 32 tie.
Second-half goals from Hulk and Sergei Semak represented a harsh lesson for Liverpool after Luis Suarez had missed a host of chances at the other end.
The game was a lively one full of chances from the start with Aleksandr Kerzhakov forcing Pepe Reina into a smart save and Suarez seeing a chance go wide inside the first two minutes.
In the fifth minute Reina pulled out another fine stop to deny the marauding Hulk who was a regular menace to the visitors with his ability to cut in from the right flank.
Although Zenit dominated the early stages, the Reds remained a threat and Suarez should have put them ahead only to fail to capitalise on an error from Nicolas Lombaerts.
The Belgian centre-back foolishly gave the ball away to Suarez but, while the striker comfortably rounded Vyacheslav Malafeev, he delayed long enough to allow Lombaerts to recover and clear.
Shortly afterwards, Hulk drilled in a shot that beat Reina only to bounce back off the woodwork to safety.
There was still time for a third chance for Suarez before the break when he tried to flick the ball in from close range after Raheem Sterling's intelligent centre but missed the target once again.
Brendan Rodgers' side began the second-half well with Glen Johnson forcing Malakeev into action following a purposeful run and Suarez measuring a good chance just wide of the post.
And with the visitors starting to look comfortable, those spurned opportunities proved costly when Hulk blasted a brilliant long-range effort into the top-left corner.
Minutes later things got worse for Liverpool when a cross from the right ran through to veteran substitute Semak and the 36-year-old midfielder tucked the ball away at the far post.
Liverpool pushed for a potentially vital away goal but it was not forthcoming and it will require a big effort to turn the tie around at Anfield next week.