A 1-1 draw with Basel was not enough to see Liverpool progress to the knockout stages of the Champions League as the Swiss side join Group B winners Real Madrid in the next round.
The Reds controlled the opening stages but a defensive lapse almost cost them dearly in the 13th minute as Martin Skrtel gifted possession to Luca Zuffi, who picked out Shkelzen Gashi in the danger zone.
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The Albanian international let fly from the edge of the penalty area, but failed to trouble Simon Mignolet between the home sticks, missing the target by some distance.
Basel took the lead in the 25th minute through Fabian Frei, who exchanged passes with Zuffi before drilling a low shot into the bottom corner in front of a stunned Kop to give the Reds a mountain to climb.
Liverpool were poor throughout the first period, much to the frustration of the expectant home support, and were fortunate that the deficit was just one come the break.
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The Swiss outfit almost had a second in the 39th minute when Dejan Lovren produced a vital block to prevent a strike from Frei finding its way into the bottom corner.
Basel did have the ball in the net again moments before half time, but Gashi's strike was ruled out for offside.
Liverpool came out for the second half with more urgency and purpose, but Basel looked just as dangerous on the counter-attack and almost killed the hosts off when Taulant Xhaka skipped past two defenders and shot narrowly wide in the 59th minute.
Disaster struck for the Reds on the hour mark as they were reduced to 10 men when Lazar Markovic was sent off for going into a challenge with his arm flailing.
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It was a contentious decision, but Basel struggled to make their numerical advantage felt, and Liverpool set the stage for an intense final 10 minutes when captain Steven Gerrard smashed a free kick into the top corner to level the game.
Liverpool played with determination in the closing stages and almost forced the issue in stoppage time when Skrtel was inches away from sliding Raheem Sterling's cross into the net, but Basel held out for the point they needed to progress and send the Reds into the Europa League.
Mark Langshaw
