Besiktas 2-1 Liverpool: Liverpool, back in the city of their triumph in 2005, were given the monumental task of needing another extraordinary revival to save themselves in the Champions League. They have found glory in such endeavour in the past but, after a dispiriting night in Istanbul, they face only ignominy should they fail to produce the improbable once again.
Defeat by a Besiktas team that began without a point or even a goal in Group A marked a new low-point for Liverpool in a campaign that has borne no resemblance to the clinical and consistently successful qualifiers of old. With three games remaining Liverpool are in peril. Bottom of the group, they cannot err again.
Recoveries are not beyond Rafael Benitez's team and they would have delivered another here had substitute Peter Crouch headed goalwards and not in the opposite direction in a frantic finale as Liverpool pressed for an equaliser.
Yet this was another puzzling display and few would invest heavily on their capacity to reach the knock-out stages now.
The backdrop to Liverpool's latest trial was more akin to a political rally than a Champions League tie between two teams desperate for their first win. Outside the stadium were banners calling for an invasion of northern Iraq and war against the Kurdish rebel organisation, the PKK, while inside a lone bugler sounded a tribute to the Turkish soldiers killed by the group in recent weeks.
Amid a sea of Turkish flags one supporter broke forth to plant the national banner in the centre of the pitch, only for the pole to break as it struck the grass.
The home side had clearly taken their lead from Porto and decided to put Liverpool on the back foot. Dynamic from the first, Besiktas believed they were denied a penalty when a clearance struck Steve Finnan's hand in the third minute, and Serdar Kurtulus went close to scoring from distance moments later.
As in Portugal, Liverpool had handed over the initiative before they had found their rhythm.
Liverpool had their opportunity in an open first half, Gokhan Zan making two valuable interceptions to deny Ryan Babel and Andriy Voronin, and the Ukrainian forward allowed Rodrigo Tello to clear off the line when he miscued horribly in front of goal.
The Turks were open for punishment, easily breached and careless in possession, but Benitez's team were similarly fallible and lacked the composure to exploit the weaknesses.
Throughout the visiting side there was an inability to deliver the simplest of passes or utilise the experience of two Champions League finals to draw the sting from limited opponents urged on by passionate support.
At times Liverpool performed like European novices, and the mess that presented Besiktas with the lead typified the performance.
What had been an immaculate challenge by Jamie Carragher on the Brazilian striker Bobo developed into a calamity when the centre-half attempted to hook clear while lying on the ground but sent the ball rebounding off Finnan. It fell kindly for Serdar Ozkan and a mishit shot deflected off the thigh of Sami Hyypia to leave Jose Reina stranded and dumb-founded in the Liverpool goal.
Though Liverpool dominated possession after the interval, they were again indebted to Carragher for another last-ditch challenge on Bobo and spared when the Brazilian shot wastefully wide when sent clear on goal by Koray Avci.
The visitors, by contrast, struggled to breach the Turkish defence, but should have levelled when Steven Gerrard volleyed wide after Voronin's knock-down found him unmarked 18 yards in front of goal.
Yossi Benayoun, a prominent replacement for Jermaine Pennant, was denied an equaliser by an offside flag against Voronin with 22 minutes remaining, and released Gerrard for what seemed Liverpool's lifeline moments later. Hakan Arikan smothered the captain's effort at close range, however, and the visitors' hopes went with it when Bobo beat Hyypia to double Besiktas' lead late on.
A superb Gerrard header restored hope for Liverpool but hope is all they now have for qualification.
Champions League Results
Group ABesiktas 2-1 Liverpool Marseille 1-1 FC Porto
Group BChelsea 2-0 Schalke 04 Rosenborg 2-0 Valencia
Group CReal Madrid 4-2 Olympiakos Werder Bremen 2-1 Lazio
Group DAC Milan 4-1 Shakhtar Donetsk Benfica 1-0 Celtic