ISTANBUL - In the city that saw Liverpool's greatest triumph of modern times, their involvement in this season's Champions League was all but ended.
Two years ago in the vast Ataturk stadium outside the city, Liverpool won their fifth European Cup.
On Wednesday, in the small but intimidating Inonu stadium, Besiktas produced their greatest European victory to leave Liverpool bottom of Group A.
Liverpool were behind early on to a Serdar Ozkan effort which deflected in off central defender Sami Hyypia.
And from then on the Anfield men toiled and laboured in an increasingly desperate attempt to avoid a humiliating defeat.
Deivson Bobo made it two with nine minutes left before Steven Gerrard's header gave Liverpool hope - but a ferocious final effort failed to save the visitors.
Liverpool's obvious need to win this clash was underlined by the inclusion of two wingers - Ryan Babel and Jermaine Pennant - in Rafael Benitez's starting line-up.
There were just two changes from the side that won at Everton on Saturday, Gerrard was back in the centre of midfield, with Mohamed Sissoko and Yossi Benayoun left out.
Liverpool had Xabi Alonso back on the bench after his metatarsal injury, with teenage defender Jack Hobbs also a substitute.
The Besiktas fans had pounded out their anthems for two hours before the match, stopping only for a minute of silence while a lone trumpeter honoured the Turkish soldiers killed in a terrorist attack at the weekend.
The volume was raised when Danish referee Claus Bo Larsen chose to ignore appeals for a penalty after three minutes when the ball struck Steve Finnan's hand.
Serdar Kurtulus volleyed just over from 20 yards a minute later before Liverpool's Andriy Voronin saw a flicked effort kicked off the line by Rodrigo Tello.
But Besiktas were ahead on 13 minutes after Jamie Carragher had produced a fine saving tackle on Bobo in the box.
His attempted clearance deflected straight to Serdar Ozkan off Javier Mascherano.
The striker slammed a deflected shot goalwards from eight yards - which hit Hyypia and wrong-footed Jose Reina.
Dirk Kuyt put Gerrard clear in the box, only for Besiktas goalkeeper Hakan Arikan to make a one-handed save at his feet.
Liverpool kept coming forward and Babel cut in from the left 30 yards out to blaze a drive over the angle on 30 minutes.
Besiktas coach Ertugrul Sagham was serving a one-match touchline ban - but it was not hindering the Turkish side. Assistant Mutlu Topcu was handling things just fine.
Besiktas started the second period intent on attack and a second killer goal. They swung the ball around quickly and had Liverpool on the back foot.
Bobo almost outpaced Carragher in one surge into the box, Reina happy to mop things up as the Brazilian lost control.
The visitors were struggling but they put together a decent move in the 58th minute when Babel's cross was nodded down by Voronin for Gerrard to drill a shot inches wide of a post.
Benayoun came on for the ineffective Pennant a minute later - a change which gave Liverpool more flair.
Babel had a shot held by Arikan, before Benayoun had a 'goal' disallowed - Voronin judged offside in the build-up.
Arikan saved from Gerrard but Liverpool were gambling and substitute Federico Higuain went clear only to be stopped by Reina on the edge of the box.
Benayoun tried to jink his way through a packed box before Lucas Leiva replaced Mascherano 15 minutes from time.
Bobo scooped the ball over from a couple of yards out but soon after the big striker was luckier when he was sent clear and guided his shot past an exposed Reina.
Peter Crouch had been standing on the line waiting to come on as the crucial second goal was being constructed. Before the restart he was on in place of Hyypia.
Gerrard gave Liverpool hope with his goal - an 84th-minute header - but despite a rousing finish, they could not find an equaliser.
