Liverpool are out of the Champions League.
The Reds needed a win against Swiss side Basel in their last group match to make the last 16 draw.
Basel drew first blood with Fabian Frei putting the visitors in front in the 25th minute.
Brendan Rodgers changed things around at half-time and brought on Lazar Markovic and Alberto Moreno.
Markovic would last less than 15 minutes before he was sent off for swinging an arm at Behrang Safari.
Steven Gerrard gave fans hope with an 81st minute free-kick but the Reds couldn't find another goal.
Manager Brendan Rodgers felt his side gave it everything towards the end
Real Madrid defeated Ludogorets in that group and go through as winners.
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Arsenal failed to make top spot in their Champions League group.
The Gunners secured a comfortable 4-1 win in Turkey against Galatasaray to finish second.
Lukas Podolski and Aaron Ramsey both scored a brace, Ramsey's second was a left-foot stunner...
Borussia Dortmund could only draw with Belgian side Anderlecht but still take top spot in the group.
Elsewhere; Juventus and Atletico Madrid ended scoreless in Turin meaning the Italian side scrape through with the Spaniards who topped the group.
Leaders Monaco and Bayer Leverkusern go through from the last group decided on the night.
