A memorable Steven Gerrard strike could not prevent Liverpool from being eliminated from the Champions League as Basel went through on Tuesday, while Juventus and Monaco also advanced to the last 16.
Liverpool are enduring a deeply disappointing season but the Anfield club knew that a win at home to Basel would take them through from Group B into the knock-out stage for the first time since 2009.
However, Basel, convincing winners when the sides met in Switzerland two months ago, needed only a point and a pinpoint strike by Fabian Frei in the 25th minute set them on their way.
An already enormous task for Liverpool appeared impossible when Lazar Markvoic was harshly sent off for a flailing arm in the direction of Behrang Safari, and although Gerrard drew them level nine minutes from time with a beautifully-flighted free-kick, the Premier League side could not find a winner.
"The expectation was to get through the group. We haven't done that because we haven't been good enough, but we'll learn from that," Liverpool manager Brendan Rodgers, whose side must now settle for the consolation of a place in the Europa League, told Sky Sports.
In contrast, Basel coach Paulo Sousa said: "We are working in this direction to achieve important things like we achieved today, which gives us the opportunity to challenge other fantastic teams."
Italian champions Juventus, knocked out at the group stage 12 months ago, are through from Group A after a 0-0 draw at home to last season's beaten finalists Atletico Madrid, who progress as group winners.
The draw for Juve means Olympiakos drop into the Europa League despite a 4-2 win in Greece against a Malmo side who finished with 10 men, with David Fuster, Alejandro Dominguez, Kostas Mitroglou and Ibrahim Afellay all scoring.
Meanwhile, it was a memorable night for Monaco, who needed only a point at home to Zenit St Petersburg to advance but a 2-0 win in the Principality, coupled with a 0-0 draw between Benfica and Bayer Leverkusen in Lisbon, saw them go through as Group C winners.
Second-half goals from defensive duo Aymen Abdennour and Fabinho secured the victory for Leonardo Jardim's Monaco, who have not qualified for the knock-out stage since they reached the final in 2004.
"Qualifying was important for me, but more so for the team, the Principality and for French football," said Jardim.
- Six out of six for Madrid -
Elsewhere, Real Madrid rounded off their Group B campaign with a 4-0 defeat of Ludogorets Razgrad at the Santiago Bernabeu, their task being facilitated by the early sending-off of Marcelinho for a handball on the line.
Cristiano Ronaldo netted the resulting penalty for his 72nd Champions League goal, leaving him just two behind Lionel Messi's record tally, before Gareth Bale, Alvaro Arbeloa and youngster Alvaro Medran added further goals.
It is just the sixth time that a team has won all six group games in the competition, the last being Madrid in 2011-12, while Carlo Ancelotti's side's Spanish record run of consecutive victories now stretches to 19.
In Group D, two stunning Aaron Ramsey strikes helped Arsenal to a morale-boosting 4-1 win against eliminated Galatasaray in Istanbul.  
Ramsey's brace came either side of two goals by Lukas Podolski, while Wesley Sneijder got one back for the Turkish side. Both of Ramsey's goals were easy on the eye, but his second - a rising 30-yard left-foot volley - was the standout moment and the Welsh midfielder later said it was "definitely the best goal I've scored".
Despite the win, Arsenal finish second in the group behind Borussia Dortmund, who drew 1-1 at home to Anderlecht, Ciro Immobile giving the hosts the lead in Germany before Aleksandar Mitrovic equalised.
"There's a little bit of frustration that we have finished runners-up, but we knew at half time we needed to score six goals without conceding," Arsenal manager Arsene Wenger said.
"Unfortunately it wasn't enough, but we finished with 13 points and did the job tonight. We came out strong and that's what I wanted from these players."
Wednesday will see the remaining two places in next Monday's last-16 draw be decided, with Roma, Manchester City and CSKA Moscow competing for one place in Group E and Sporting Lisbon and Schalke fighting it out for a place from Group G.
In addition, Barcelona and Paris Saint-Germain clash in a shoot-out to decide who finishes top of Group F.
Source: AFP