Liverpool have been eliminated from the Europa League following a 5-4 penalty shootout defeat at the hands of Besiktas in the second leg of their last-32 tie at the Ataturk Olympic Stadium this evening.
The Anfield club had earlier looked on course to edge through with a 1-0 aggregate win, but Tolgay Arslan's second-half strike saw the game forced into extra time and penalties after a 1-1 draw.
Unfortunately for Liverpool fans, Dejan Lovren could not build on his teammates' clinical penalty attempts, as he blazed his effort over Cenk Gonen's crossbar to end his side's ambitions of claiming European glory this season.
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The game began in rather tense circumstances as both sides wrestled for a foothold, with Olcay Sahan producing some good work to seek out Demba Ba, who was thwarted by some good defensive work from Lovren.
Liverpool's first chance did not arrive until the 20th minute, when Alberto Moreno found Raheem Sterling, leaving the young winger to draw a strong save from Gonen.
Some good play from Daniel Sturridge saw him play in Sterling just a few minutes later, but his first touch was poor, allowing the Besiktas defence to recover in time to make the clearance.
The Reds passed up a perfect chance to move in front in the 31st minute after Mario Balotelli robbed a defender, but Sturridge's effort was too tame to get past Gonen who saved comfortably.
Besiktas sensed danger at the interval and they went in search of a vital goal in the second half, with Serdar Kurtulus seeking an effort from distance that was well saved by Simon Mignolet.
With Liverpool's defence standing firm, the Turkish side's main efforts came from distance, Gokhan Tore coming close with a curling shot that just evaded Mignolet's top corner.
The home team grew increasingly dominant and they grabbed a goal to bring them back into the contest in the 72nd minute, as Ba picked out Arslan who curled neatly into the Liverpool goal.
Besiktas almost grabbed a winning goal in the dying embers of the game, only for Ba to see his shot cannon back off the crossbar, leaving the game to head into extra time.
Liverpool stopper Mignolet had a busy second half and he was brought into the fray again, this time as he stood tall to keep out Ba's shot at his near post, before Martin Skrtel stole in to clear away any remaining danger.
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The Reds rarely threatened in the extra period and Sturridge spurned his side's best opportunity, having given up possession far too easily with Liverpool seeking to break at pace.
Former Chelsea frontman Ba remained a nuisance in the closing minutes of the additional period and he came close with attempts that were skewed off target, before the referee blew the whistle to signal a penalty shootout.
Both sides were clinical from the spot up until Lovren saw his attempt fly over the bar, sending Brendan Rodgers and his men out of the tournament.
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