Liverpool paid for profligacy as goals from Hulk and Sergei Semak gave Zenit St Petersburg a commanding lead in the first leg of their Europa League tie.
Luis Suarez was guilty of several misses including a shot from five yards out and a curling effort just wide.
Hulk had already hit the post in the first half but smacked in a swerving shot after 70 minutes.
And three minutes later Semak tucked in at the back post to give Liverpool an uphill task in the second leg.
Suarez, who is Liverpool's top scorer this season, also failed to test the Zenit keeper despite being clean through, and shot wide with two other chances.
It was far from one-way traffic, though, with Pepe Reina having to make several early saves.
The result was perhaps harsh on Liverpool in front of a fiercely vocal and partisan crowd, who did not appear to direct any racist chanting towards Liverpool's players despite pre-match fears from the English side.
The game's narrative had a certain familiarity to it, coming three days after a 2-0 defeat by West Brom in which the Baggies grabbed two late goals.
Like that Premier League match, Liverpool were without the cup-tied Daniel Sturridge. On this occasion it was Hulk, rather than Romelu Lukaku, who showed Suarez how to finish with a smartly-taken goal.
The Brazilian striker, who has struggled since his £32m transfer from Porto in September, tormented Liverpool in an entertaining opening 15 minutes which featured plenty of chances for both teams - despite the subzero temperatures.
First, Hulk crossed for Aleksandr Kerzhakov and then took a left-footed shot himself, with Reina saving well on both occasions.
In between those opportunities, Suarez had fired wide after breaking free but he should have given Liverpool the lead when he intercepted Nicolas Lombaerts' pass in the Russian defender's half, but over-ran the ball when attempting to take it around the keeper Vyacheslav Malafeev.
There were further shaky moments for both defences before the first half was done. Hulk's shot slipped through Reina's grasp and hit the post, while Suarez missed the target from five yards out after Raheem Sterling had gathered Joe Allen's floated cross.
The tricky pitch hardly helped matters, and Allen - recalled to the side in place of Lucas - struggled to control and distribute the ball in his customary fashion.
With opportunities blundered, there was a real danger for Liverpool that, having been made to pay for similar wastefulness on several occasions this season, they might suffer again.
That feeling grew early in the second half when, first, Glen Johnson made a barnstorming run from his own half only to be denied by Malafeev and then Suarez missed the target once more when he tried to curl his shot into the corner from the edge of the box.
And so it came to pass after 70 minutes. Jordan Henderson lost possession and when the ball was fed to Hulk he advanced on goal before cracking a shot into the top corner from the edge of the box.
Two minutes later Zenit were two goals to the good as Martin Skrtel failed to clear Aleksandr Anyukov's cross from the right and Johnson was nowhere to be seen as substitute Semak converted at the back post.
Suarez tested Malafeev once more with a free-kick from the edge of the box, but despite creating so much, Liverpool again lacked a killer instinct.
Liverpool boss Brendan Rodgers: "Luis Suarez could have had a hat-trick by half-time but it wasn't his night. He's been brilliant for us all season, but after the first one on one, he still kept going and that's the positive we take into the next game. If we can be solid and secure, we can create chances to score and we saw enough of that tonight on a difficult pitch.
"There's no doubt the supporters will give us a chance [at Anfield], and the next goal is very important. If we get it, it opens up the tie but we have to make sure that we are secure as a group and if we are then we can create chances."
Live Text Commentary
Full Time The referee signals the end of the game.
90:00 +1:21Short corner worked by Axel Witsel.
88:20Foul by Viktor Faitzulin on Sanchez Jose Enrique, free kick awarded. Direct free kick taken by Sanchez Jose Enrique.
85:37Givaldinho Hulk takes a short corner.
83:08Shot comes in from Luis Suarez from the free kick, save by Viacheslav Malafeev.
83:08 BookingBooking Carlos Luis Neto shown a yellow card.
82:29Carlos Luis Neto concedes a free kick for a foul on Luis Suarez.
81:53Corner from the right by-line taken by Stewart Downing, save by Viacheslav Malafeev.
81:36 SubstitutionSubstitution Viktor Faitzulin joins the action as a substitute, replacing Alexander Kerzhakov.
77:21 SubstitutionSubstitution Raheem Sterling leaves the field to be replaced by Leiva Lucas.
74:40Givaldinho Hulk decides to take the corner short.
74:18Givaldinho Hulk takes a inswinging corner from the right by-line to the near post, clearance made by Jamie Carragher.
71:34The assist for the goal came from Roman Shirokov.
71:34 Goal scoredGoal - Sergei Semak - Zenit St P 2 - 0 Liverpool Sergei Semak finds the back of the net with a goal from close range high into the middle of the goal. Zenit St Petersburg 2-0 Liverpool.
69:02 Goal scoredGoal - Givaldinho Hulk - Zenit St P 1 - 0 Liverpool Givaldinho Hulk gets on the score sheet with a brilliant goal from outside the penalty area to the top left corner of the goal. Zenit St Petersburg 1-0 Liverpool.
65:14Stewart Downing takes a inswinging corner from the right by-line to the near post, clearance by Carlos Luis Neto.
63:29Roman Shirokov concedes a free kick for a foul on Stewart Downing. Jamie Carragher restarts play with the free kick.
59:49Luis Suarez has an effort at goal from just outside the box which goes wide of the right-hand upright.
58:58Martin Skrtel restarts play with the free kick.
58:58 BookingBooking Tomas Hubocan is shown a yellow card for unsporting behaviour.
Foul by Tomas Hubocan on Steven Gerrard, free kick awarded.
58:00Aleksandr Aniukov challenges Raheem Sterling unfairly and gives away a free kick. Martin Skrtel takes the free kick.
53:12 SubstitutionSubstitution Sergei Semak on for Miguel Danny.
52:56Shot by Axel Witsel from a long way out goes over the net.
51:25Foul by Nicolas Lombaerts on Stewart Downing, free kick awarded. Steven Gerrard crosses the ball from the free kick right-footed from right wing, Roman Shirokov makes a clearance.
49:09Corner taken by Stewart Downing from the left by-line played to the near post, Nicolas Lombaerts makes a clearance.
48:36Glen Johnson takes a shot. Save made by Viacheslav Malafeev.
46:51The referee blows for offside against Raheem Sterling. Free kick taken by Carlos Luis Neto.
45:01The match restarts for the second half.
45:00 +2:06 Half timeHalf Time The referee calls an end to the first half.
45:00 +1:42Free kick awarded for a foul by Luis Suarez on Axel Witsel. Axel Witsel takes the free kick.
45:00 +1:12Givaldinho Hulk takes a shot from 30 yards. Comfortable save by Jose Reina.
44:38Luis Suarez challenges Carlos Luis Neto unfairly and gives away a free kick. Direct free kick taken by Carlos Luis Neto.
44:09Stewart Downing has an effort at goal from outside the box which misses left.
41:27Jordan Henderson gives away a free kick for an unfair challenge on Axel Witsel. Nicolas Lombaerts restarts play with the free kick.
40:06Axel Witsel gives away a free kick for an unfair challenge on Sanchez Jose Enrique. Sanchez Jose Enrique takes the direct free kick.
39:35Glen Johnson has an effort at goal from close range which goes wide left of the target.
38:22The ball is sent over by Carlos Luis Neto, Jose Reina makes a comfortable save.
37:01Sanchez Jose Enrique fouled by Axel Witsel, the ref awards a free kick. Sanchez Jose Enrique takes the free kick.
27:17Axel Witsel takes a shot. Save made by Jose Reina.
26:49Axel Witsel takes a shot. Save made by Jose Reina.
24:27The referee blows for offside against Luis Suarez. Igor Denisov restarts play with the free kick.
23:44Luis Suarez gives away a free kick for an unfair challenge on Aleksandr Aniukov. Viacheslav Malafeev takes the free kick.
22:31Martin Skrtel challenges Axel Witsel unfairly and gives away a free kick. Direct free kick taken by Axel Witsel.
21:10Steven Gerrard takes the inswinging corner, Foul by Martin Skrtel on Tomas Hubocan, free kick awarded. Viacheslav Malafeev restarts play with the free kick.
18:38The ball is sent over by Givaldinho Hulk, Jordan Henderson manages to make a clearance.
18:00Givaldinho Hulk takes a outswinging corner to the near post, clearance made by Stewart Downing.
16:10Free kick taken by Igor Denisov.
16:10 BookingBooking Martin Skrtel shown a yellow card.
16:02Foul by Martin Skrtel on Roman Shirokov, free kick awarded.
11:56Nicolas Lombaerts challenges Jordan Henderson unfairly and gives away a free kick. Free kick crossed by Steven Gerrard.
8:43Givaldinho Hulk challenges Sanchez Jose Enrique unfairly and gives away a free kick. Sanchez Jose Enrique restarts play with the free kick.
5:39The offside flag is raised against Luis Suarez. Aleksandr Aniukov takes the direct free kick.
4:52Short corner taken by Aleksandr Aniukov.
4:29Givaldinho Hulk takes a shot. Save by Jose Reina.
2:40Luis Suarez is flagged offside by the assistant referee. Nicolas Lombaerts takes the direct free kick.
1:59Luis Suarez has an effort at goal from deep inside the area missing to the right of the goal.
1:02Alexander Kerzhakov takes a shot. Save made by Jose Reina.
0:34Short corner worked by Givaldinho Hulk.
0:00The game kicks-off.
Live text and data provided by The Press Association
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