Liverpool's hopes of qualifying for the knockout stages of the Europa League hang in the balance after losing to Guus Hiddink's Anzhi Makhachkala.
A goal from Anzhi's 6ft 8in Lacina Traore right on half-time was enough to send Brendan Rodgers' young and largely inexperienced side to defeat in Moscow.
The Ivorian striker produced a moment of magic to loop the ball over Brad Jones and decide the Group A match.
Jordan Henderson spurned the best of Liverpool's chances but Anzhi held on.
Reds records fall
- This was Liverpool's first defeat away from home in a Uefa Cup or Europa League group game
- This was also only Liverpool's third defeat in their past 23 European games
- Stewart Downing has appeared in all eight of Liverpool's European games this season
- Liverpool had won all three away games in Europe this season before the trip to Anzhi
- In their eight games in the competition this season they have scored 14 goals with eight conceded
- Source: Opta
On the face of it, this was another disappointing defeat for Liverpool, who slip off the top of the group.
New leaders Anzhi are one point clear with two rounds of matches remaining, while Swiss side Young Boys have moved alongside the second-placed Reds on six points following their 3-2 win at Udinese.
But, although the ongoing problem of a chronic failure to turn possession into points remained, there were signs of encouragement with many of Rodgers' young players largely holding their own in a difficult environment.
It was a bracing night in Moscow, one that called for the presence of men and not boys. It said much of Liverpool's current predicament that Jonjo Shelvey was one of the most experienced players in Rodgers' line-up but throughout he led from the front, dictating play and setting the tempo with an assurance that belied his 21 years.
This competition has been something of a testing ground for Liverpool's youngsters, with Raheem Sterling, Andre Wisdom and Suso announcing their respective arrivals with a series of impressive performances. Youth was to the fore again with 19-year-old Conor Coady handed his debut alongside 18-year-old striker Adam Morgan.
Joe Cole, celebrating his 31st birthday, had little impact as the youngsters drove Liverpool on. The best of the chances fell to Henderson after 23 minutes following a clever spin and perfectly timed through ball from Morgan.
The England midfielder found himself with only goalkeeper Georgi Gabulov to beat but, rather than shoot, Henderson hesitated and tried to slide the ball inside for Cole only for Joao Carlos to intercept.
The Russians had shown a glimpse of their ability after 35 minutes when Liverpool goalkeeper Brad Jones was forced to turn Samuel Eto's fierce shot over the bar, after former Chelsea winger Yuri Zhirkov had robbed Wisdom near the halfway line.
On both sides, the football was muscular and committed but devoid of the finesse to create the breakthrough. Individualism appeared the most likely source of joy and so it proved.
Traore shattered the mediocrity with the first half's single moment of brilliance, hooking the ball over Sebastien Coates's head with his right foot before lifting a bouncing ball high past Jones with his left to snatch the lead with the last kick before the interval.
Morgan fired into the side netting after the break, but Anzhi began the second half with more pace and purpose than they had displayed at almost any time in the first.
Eto'o went close with a curling right-foot shot from distance before Rasim Tagirbekov fired a fizzing left-foot shot narrowly wide.
The Anzhi left-back was at the heart of the action again with 15 minutes remaining as Troare headed his pin-point cross at goal, only for Jones to produce yet another impressive save.
Liverpool kept pushing, however. Suso, on as a substitute, tested Gabulov with a dipping shot but Cole was unable to convert the rebound.
Traore should have killed the match on 78 minutes when he raced onto Jucilei's delightful through-ball only to pull his shot a foot wide of Jones's left-hand post with only the Liverpool goalkeeper to beat. The Premier League club pushed for an equaliser, but Anzhi stood firm.
Live text and stats
Thursday, 8 November 2012
- Anzhi Makhachkala 51%
- Liverpool 49%
Attempts on target
- Anzhi Makhachkala 8
- Liverpool 3
Attempts off target
- Anzhi Makhachkala 4
- Liverpool 5
- Anzhi Makhachkala 1
- Liverpool 2
- Anzhi Makhachkala 7
- Liverpool 11
- Final Result
- Full Time
- 90:00+3:31 The final whistle goes and the game is over.
- 90:00+3:13 Jonjo Shelvey produces a cross.
- 90:00+1:17 Substitution Shamil Lakhiyalov on for Mehdi Carcela-Gonzalez.
- 89:21 Jon Flanagan sends in a cross, Jordan Henderson has an effort at goal from the edge of the box that misses to the right of
- 88:43 Unfair challenge on Jordan Henderson by Fedor Smolov results in a free kick. Jordan Henderson takes the free kick.
- 87:42 Indirect free kick taken by Christopher Samba.
- 87:42 Booking Caution for Jonjo Shelvey.
- 87:37 Silva Jucilei fouled by Jonjo Shelvey, the ref awards a free kick.
- 86:36 Jonjo Shelvey has an effort at goal from outside the penalty area which goes wide right of the goal.
- Correction - 85:41 Effort from outside the area by Jonjo Shelvey goes wide right of the goal.
- 85:34 Arseni Logashov challenges Oussama Assaidi unfairly and gives away a free kick. Jordan Henderson takes the free kick.
- 85:02 Fedor Smolov takes a shot. Save made by Brad Jones.
- 83:16 The assistant referee signals for offside against Daniel Pacheco. Free kick taken by Vladimir Gabulov.
- 82:26 Silva Jucilei takes a shot. Blocked by Jamie Carragher.
- 82:00 Daniel Pacheco takes a short corner.
- 81:43 Stewart Downing crosses the ball, Rasim Tagirbekov makes a clearance.
- 79:31 Substitution Fedor Smolov is brought on as a substitute for Lacina Traore.
- 79:31 Shot from just outside the area by Jordan Henderson misses to the right of the target.
- 77:35 Effort from the edge of the box by Lacina Traore goes wide of the right-hand upright.
- 75:50 Joe Cole takes a shot. Save made by Vladimir Gabulov. Corner taken short by Daniel Pacheco.
- 75:50 Substitution Oussama Assaidi on for Joe Cole.
- 75:50 Jesus Fernandez Saez takes a shot from 18 yards. Save by Vladimir Gabulov.
- 75:15 The ball is crossed by Arseni Logashov, Lacina Traore has a headed effort at goal, Brad Jones makes a save.
- 74:01 Jesus Fernandez Saez challenges Samuel Eto'o unfairly and gives away a free kick. Arseni Logashov takes the direct free kick.
- 73:35 The ball is sent over by Stewart Downing, Pinto Joao Carlos makes a clearance.
- 72:32 Unfair challenge on Arseni Logashov by Daniel Pacheco results in a free kick. Christopher Samba takes the free kick.
- 70:32 Free kick awarded for a foul by Lacina Traore on Jamie Carragher. Jamie Carragher takes the free kick.
- 69:19 Free kick awarded for an unfair challenge on Jordan Henderson by Mbark Boussoufa. Jamie Carragher takes the indirect free
- 68:15 Jonjo Shelvey gives away a free kick for an unfair challenge on Lacina Traore. Mbark Boussoufa restarts play with the free
- 64:06 Free kick taken by Pinto Joao Carlos.
- 64:06 Booking Caution for Jon Flanagan.
- 64:01 Jon Flanagan gives away a free kick for an unfair challenge on Rasim Tagirbekov.
- 63:30 Yury Zhirkov produces a left-footed shot from just outside the box that misses to the right of the target.
- 60:18 Substitution Jesus Fernandez Saez is brought on as a substitute for Conor Coady.
- 60:18 Substitution Daniel Pacheco is brought on as a substitute for Adam Morgan.
- 60:18 Jamie Carragher fouled by Lacina Traore, the ref awards a free kick. Jamie Carragher takes the indirect free kick.
- 59:12 Lacina Traore has a shot on goal from outside the area which misses left.
- 57:16 Shot by Samuel Eto'o. Save made by Brad Jones.
- 54:31 Christopher Samba fouled by Jon Flanagan, the ref awards a free kick. Pinto Joao Carlos takes the indirect free kick.
- 54:01 Stewart Downing delivers the ball, Pinto Joao Carlos manages to make a clearance.
- 51:18 Effort from deep inside the area by Adam Morgan misses to the left of the target.
- 48:52 Free kick awarded for an unfair challenge on Lacina Traore by Conor Coady. Mbark Boussoufa takes the indirect free kick.
- 46:17 The referee blows for offside against Joe Cole. Free kick taken by Vladimir Gabulov.
- 45:01 The referee gets the second half underway.
- Half Time
- 45:00+2:13 The whistle is blown to end the first half.
- 45:00+0:48 Mbark Boussoufa provided the assist for the goal.
- 45:00+0:48 GOAL - Lacina Traore:Anzhi Makhachkala 1 - 0 Liverpool Lacina Traore gets on the score sheet with a goal from just inside the penalty area high into the middle of the goal. Anzhi
Makhachkala 1-0 Liverpool.
- 44:07 Andre Wisdom crosses the ball.
- 41:51 Unfair challenge on Joe Cole by Pinto Joao Carlos results in a free kick. Stewart Downing produces a cross, Header by Joe
Cole from deep inside the penalty area misses to the left of the target.
- 40:26 Jordan Henderson takes a shot. Save made by Vladimir Gabulov.
- 39:57 The ball is sent over by Jordan Henderson, clearance by Christopher Samba.
- 35:39 Corner taken by Mbark Boussoufa.
- 35:37 Free kick awarded for a foul by Jon Flanagan on Rasim Tagirbekov. Mbark Boussoufa takes the direct free kick.
- 35:12 Effort on goal by Samuel Eto'o from 12 yards. Save made by Brad Jones.
- 29:56 Effort on goal by Mehdi Carcela-Gonzalez from just inside the area clears the crossbar.
- 29:36 Lacina Traore takes a shot. Blocked by Jamie Carragher.
- 28:35 Free kick crossed right-footed by Mbark Boussoufa.
- 28:35 Substitution Mehdi Carcela-Gonzalez replaces Odil Ahmedov.
- 28:35 Jamie Carragher gives away a free kick for an unfair challenge on Mbark Boussoufa.
- 27:39 The ball is swung over by Jonjo Shelvey, comfortable save by Vladimir Gabulov.
- 22:55 Free kick awarded for an unfair challenge on Lacina Traore by Andre Wisdom. Free kick taken by Rasim Tagirbekov.
- 20:18 The ball is swung over by Stewart Downing, clearance made by Christopher Samba.
- 16:31 Lacina Traore produces a cross, Brad Jones makes a save.
- 10:31 The referee blows for offside. Pinto Joao Carlos restarts play with the free kick.
- 9:19 Jordan Henderson gives away a free kick for an unfair challenge on Odil Ahmedov. Free kick taken by Christopher Samba.
- 8:54 Stewart Downing delivers the ball.
- 7:38 Free kick awarded for a foul by Pinto Joao Carlos on Joe Cole. Jordan Henderson takes the indirect free kick.
- 4:52 Rasim Tagirbekov takes a shot. Save by Brad Jones.
- 0:00 The match has kicked off.
Live text and data provided by The Press Association.