Liverpool have been dumped out of the 2014/15 UEFA Champions League following their 1-1 draw with FC Basel at Anfield.
The Reds required a victory over the Swiss champions to join Real Madrid in the Round of 16 but were unsuccessful in their pursuit of making it through on their return to Europe's top flight.
Fabian Frei made life difficult for Brendan Rodgers' men when firing home from 20 yards in the 25th minute before Lazar Markovic's sending off just after the hour-mark heaped more pressure on the Merseysiders.
Steven Gerrard attempted to lift his side by netting with an 81st-minute free-kick but the Reds were unable to find the winning goal needed to progress to the knockout phase of the competition.
Basel will join Real in the next stage after the reigning European champions comfortable defeated Bulgarian minnows Ludogorets Razgrad 4-0 at the Santiago Bernabeu.
Cristiano Ronaldo netted his 30th goal in all competitions this season when converting from the penalty spot in the 20th minute after Marcelinho had been sent off for handling the ball in the area.
Gareth Bale added a second seven minutes before the break prior to second-half goals from Alvaro Arbeloa and youngster Alvaro Medran - the latter opening his Champions League account - to give Carlo Ancelotti's side six wins from six group stage fixtures.
In Group D, Arsenal bounced back from their shock loss at Stoke City on the weekend by comfortably accounting for Galatasaray 4-1 in Istanbul.
Lukas Podolski gained a rare start and did not disappoint when thundering home in just the third minute before a brace from Aaron Ramsey - the second a stunner from 30 yards - had the Gunners in complete control.
Wesley Sneijder pulled one back late for Gala but Podolski was able to grab a second to give Arsene Wenger's side a second-placed finish behind Borussia Dortmund.
The German side drew 1-1 with Anderlecht at home to maintain their place on top of the table with the Belgians dropping into the Europa League along with Liverpool.
Olympiakos beat Malmo 4-2 in Athens to finish in third spot while Juventus and Atletico Madrid drew 0-0 in Turin which saw the Spaniards remain in top spot in Group A.
And in Group C, Monaco edged into top spot with a 2-0 home win over Zenit Saint Petersburg as Bayer Leverkusen gave up their mantle as the group's best side after being held to a 0-0 draw by Benfica.
Wednesday night sees Manchester City needing to beat AS Roma in Italy to move through to the knockout phase as Barcelona host Paris Saint-Germain while Sporting Lisbon travel to Chelsea and Bayern Munich are at home to CSKA Moscow.
2014/15 UEFA Champions League - group stage scores
Group A
Olympiakos (GRE): 4 (David Fuster 22', Alejandro Dominguez 63', Kostas Mitroglou 87', Ibrahim Afellay 90') Malmo (SWE): 2 (Simon Kroon 59', Markus Rosenberg 81') Karaiskakis Stadium, Athens, Greece - 27,562
Juventus (ITA): 0 Atletico Madrid (SPN): 0 Juventus Stadium, Turin, Italy - 39,219
*Atletico Madrid and Juventus progress to Round of 16 *Olympiakos drop into Europa League
Group B
Liverpool (ENG): 1 (Steven Gerrard 81', red card: Lazar Markovic 61') FC Basel (SUI): 1 (Fabian Frei 25') Anfield, Liverpool, England - 43,290
Real Madrid (SPN): 4 (Cristiano Ronaldo (p) 20', Gareth Bale 38', Alvaro Arbeloa 79', Alvaro Medran 88') Ludogorets Razgrad (BUL): 0 (red card: Marcelinho 19') Santiago Bernabeu, Madrid, Spain - 58,393
*Real Madrid and FC Basel progress to Round of 16 *Liverpool drop into Europa League
Group C
Monaco (FRA): 2 (Aymen Abdennour 63', Fabinho 89') Zenit Saint Petersburg (RUS): 0 Stade Louis II, Monaco, France - 11,319
Benfica (POR): 0 Bayer Leverkusen (GER): 0 Estadio da Luz, Lisbon, Portugal - 17,564
*Monaco and Bayer Leverkusen progress to Round of 16 *Zenit Saint Petersburg drop into Europa League
Group D
Galatasaray (TUR): 1 (Wesley Sneijder 88') Arsenal (ENG): 4 (Lukas Podolski 3'/90+2', Aaron Ramsey 10'/29') Turk Telekom Arena, Istanbul, Turkey - 20,590
Borussia Dortmund (GER): 1 (Ciro Immobile 58') Anderlecht (BEL): 1 (Aleksandar Mitrovic 84') Westfalenstadion, Dortmund, Germany - 65,851 *Borussia Dortmund and Arsenal progress to Round of 16 *Anderlecht drop into Europa League
