Liverpool are out of the UEFA Champions League (UCL) after playing a 1-1 draw with Basel on a night they needed a win.
Basel took an early lead through Fabien Frei before Reds substitute Lazar Markovic was sent off midway through the second half.
Steven Gerard’s free-kick gave the home side hope with 10 minutes remaining but the Swiss held on for a well-deserved draw.
The result sees Basel secure second spot in Group B, with the Reds confined to the Europa League knockout stages.
In the other group game, Real Madrid set a Spanish record for consecutive victories in all competitions of 19 when they beat visiting Ludogorets 4-0.
Real surpassed the previous record they jointly held with Barcelona, who won 18 matches in a row between October 2005 and January 2006.
Real, the European champions last failed to win when they were beaten 2-1 by city rivals Atletico Madrid in a La Liga game in September.
They can make it 12 straight victories in Spain’s top flight when they play at Almeria on Friday before heading to the Club World Cup in Morocco.
In Turin, Juventus got the point they needed against Atletico Madrid, as both teams go through to the Round of 16.
Juve needed at least a draw against Atletico, who had already qualified for the knockout stages, to progress as Olympiakos beat Malmo 4-2 in Greece.
The home side had a scare when Gabi hit the post from a corner but the Italian champions did enough to seal progress.
Monaco qualified for the knockout phase by defeating Zenit 2-0 to finish top of Group C.
Aymen Abdennour headed home a free kick from Yannick Ferreira-Carrasco in the 63rd minute while Brazilian fullback Fabinho added a second goal in the 89th minute.
Zenit finished third in the group behind Bayer Leverkusen, who drew 0-0 with Benfica.
Borussia Dortmund and Arsenal already sealed qualification from Group D before Tuesday’s games.
Juventus 0-0 Atletico Madrid
Olympiakos 4-2 Malmo FF
Liverpool 1-1 Basel
Real Madrid 4-0 Ludogorets
Benfica 0-0 Bayer Leverkusen
Monaco 2-0 Zenit
Borussia Dortmund 1-1 Anderlecht
Galatasaray 1-4 Arsenal