Liverpool FC 1-1 FC Basel 1893 Fabian Frei's first-half strike proved crucial at Anfield, the Swiss champions holding on for second place in Group B despite a late Steven Gerrard equaliser.
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• Basel draw secures second place in Group B
• Fabian Frei goal (25) sends Basel into last 16 for first time since 2011/12
• Steven Gerrard's late free-kick (81) not enough for Liverpool
• Reds substitute Lazar Marković sent off on hour
• Round of 16 draw takes place in Nyon at 12.00CET on 15 December
FC Basel 1893 secured their place in the last 16 of the UEFA Champions League with a draw at Anfield that ended the hopes of ten-man Liverpool FC.
The Reds had needed a victory to overtake their opponents but Paulo Sousa's men performed impressively and claimed the point they required through Fabian Frei's first-half goal. Steven Gerrard equalised with a brilliant late free-kick but Liverpool, reduced to ten men by the dismissal of substitute Lazar Marković, could not force the crucial second goal.
For Liverpool, this contest had obvious parallels with their last group game against Olympiacos FC ten years and a day ago, a famous 3-1 victory that provided the launchpad for their triumphant run to Istanbul. This time the comeback came too late and they exit the competition with just one win from six games.
It was Basel, roared on by their noisy fans, who took control from the early stages when some uncertain Martin Škrtel defending let in Shkelzen Gashi for an opportunity he sliced wide.
At the other end the tone of a frustrating first half for Liverpool was set when Raheem Sterling failed to find Gerrard inside the Basel box. Liverpool's passing lacked fluency and a sharper Basel carried the greater threat. Marco Streller had a close-range shot blocked and after 25 minutes Basel took the lead.
It was a well-worked goal as Frei twisted away from Joe Allen and fed Luca Zuffi who teed him up to arrow a first-time shot across Simon Mignolet and into the bottom corner. The Switzerland midfielder had already scored at Old Trafford and White Hart Lane and now has a goal in front of the Kop to add to his collection.
Buoyed, Basel soon threatened a second, with Streller hitting an acrobatic volley wide after Taulant Xhaka picked him out unmarked at the far post.
Brendan Rodgers' reaction was a half-time double substitution as Marković and Albert Moreno came on. This meant Sterling moved into the central striking role but Liverpool remained frustrated and Xhaka nearly killed off the contest with a shot just past the far post.
On the hour Liverpool's night went from bad to worse with Marković dismissed for catching Behrang Safari in the face with his trailing hand. Yet Gerrard gave them hope when he curled in a superb free-kick in off the post with nine minutes remaining.
That set up a tense finish when either side might have scored again, notably the ten men of Liverpool. Henderson saw Tomáš Vaclík save his deflected header on the goal-line but when the keeper pushed aside another Henderson effort in added time, Basel's job was done.