Luis Suarez slotted in a free-kick before Joe Allen prodded home. Suarez struck a sensational second set-piece but Liverpool were unable to gain the crucial fourth goal they needed.
The big-spending Russian champions continued to look suspect against wave after wave of Liverpool attacks and Vyacheslav Malafeev was beaten again just before the break after Allen volleyed in a rebound from his own header after an excellent one-two between rampaging left-back Jose Enrique and the improving Jordan Henderson.
Urged on by the typically passionate support as they attacked the Kop end, Liverpool started quickly after the interval and demanded that referee Bjorn Kuipers point to the penalty spot after Tomas Hubocan appeared to clumsily handle the ball.
The Dutchman rejected those claims but Liverpool took matters into their own hands when Suarez rifled in another unstoppable free-kick that curled beautifully inside Malafeev's left-hand post.
In a frantic next few minutes, Steven Gerrard volleyed into the floor, substitute Jonjo Shelvey fired agonisingly into the side-netting and another Suarez dead ball was pushed to safety.
Liverpool's anthem 'You'll Never Walk Alone' rang around Anfield as the crowd tried to push their players on at the death, but another chance could not be crafted as Zenit - who will meet Swiss side FC Basel in the last 16 - held on to win courtesy of Hulk's away goal.
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