Liverpool were left to regret a string of missed chances as Russian champions Zenit St Petersburg completed a convincing 2-0 victory in their Europa League last-32, first leg match on Thursday.
Two goals in three minutes midway through the second half turned the tide in Zenit's favour after both sides had squandered a hatful of opportunities on a badly churned-up pitch in Russia's former Imperial capital.
First, big-money Brazilian signing Hulk put the Russians ahead in the 69th minute with a blistering shot from the edge of the area which just clipped Martin Skrtel to wrong-foot Liverpool goalkeeper Pepe Reina.
Then on 72 minutes, Sergei Semak turned up the heat on Liverpool when he ghosted in behind Skrtel and Glenn Johson to arrive unmarked on the left to clinically dispatch Aleksandr Anyukov's cross from the right past Reina.
For Liverpool, Luis Suarez was the chief culprit and could have a hat-trick in the first half alone but for some profligate finishing.
But his worst miss came early in the second half as a good collective move orchestrated by Steven Gerrard ended with Stewart Downing teeing up Suarez in front of goal but he curled his shot casually wide.
That leaves Liverpool with an uphill struggle in the home leg at Anfield.
Racist taunts from some of Zenit's more vociferous fans, which Liverpool officials had feared after recent incidents at the club, failed to materialise.
In the night's other early match, also in Russia, Anzhi Makhachkala beat Germany's Hannover 3-1, despite falling behind to Szabolcs Huszti's 22nd minute strike.
Samuel Eto'o put them back on terms, the former Barcelona and Inter Milan striker tapping in a pass from Willian, and Odil Ahmedov put them ahead just after the break before Moroccan midfielder Mbark Boussoufa sealed it in the 64th minute.