The first half of Match Day 6 of the 2015/16 UEFA Champions League took place around Europe on Tuesday night.
On a dramatic evening in Germany, Manchester United's fate was sealed as they were beaten 3-2 by Wolfsburg at the Volkswagen Arena.
Louis van Gaal's Red Devils needed to avoid defeat and hope that PSV Eindhoven did not beat CSKA Moscow in Holland, but neither of those things occurred in what was a catastrophic result for the English powerhouse.
Anthony Martial had United ahead on 10 minutes before Naldo and Vieirinha saw Wolfsburg go into the break 2-1 up, after the visitors had a goal disallowed for offside just before the half-time whistle.
An own-goal from Josuha Guilavogui had United back on level terms in the 82nd minute but Naldo immediately responded for Die Wolfe to see Dieter Hecking's side finish top of Group B.
Joining them in the Round of 16 is PSV who came from a goal down to beat CSKA 2-1 at the Philips Stadion.
Sergei Ignashevich put the Russians ahead from the spot in the 76th minute but Luuk de Jong levelled within two minutes before Davy Propper saw off the challenge of the visitors to see PSV claim second spot.
In Group A, Real Madrid made light work of Swedish club Malmo with a remarkable 8-0 result.
Cristiano Ronaldo scored four times to set a new Champions League group stage record of 11 goals while Karim Benzema helped himself to a hat-trick as Rafa Benitez's Blancos obliterated their rivals.
Zlatan Ibrahimovic became Paris Saint-Germain's leading scorer in Europe when he netted in their routine 2-0 victory over Shakhtar Donetsk in the other group fixture which sees the French giants join Madrid in the next stage.
Group D saw Manchester City stage a stunning comeback to beat Borussia Monchengladbach 4-2 at the Etihad Stadium.
A brace from Raheem Sterling and late goal from Wilfried Bony saw Manuel Pellegrini's men overtake Juventus, who lost 1-0 at Sevilla, and clinch top position in their group.
And in Group C, Atletico Madrid beat Benfica 2-1 in Portugal to remain top of the table as Galatasaray drew 1-1 with Astana to claim third spot and a place in the Europa League.
2015/16 UEFA CHAMPIONS LEAGUE - GROUP STAGE SCORES
Group A
Real Madrid (SPN): 8 (Karim Benzema 12'/24'/74', Cristiano Ronaldo 39'/47'/50'/59', Mateo Kovacic 70')
Malmo (SWE): 0
Santiago Bernabeu, Madrid, Spain - 60,663
Paris Saint-Germain (FRA): 2 (Lucas Moura 57', Zlatan Ibrahimovic 86')
Shakhtar Donetsk (UKR): 0
Parc des Princes, Paris, France - 44,408
Group B
Wolfsburg (GER): 3 (Naldo 14'/84', Vieirinha 29')
Manchester United (ENG): 2 (Anthony Martial 10', Josuha Guilaovgui (OG) 82')
Volkswagen Arena, Wolfsburg, Germany - 26,400
PSV Eindhoven (NED): 2 (Luuk de Jong 78', Davy Propper 86')
CSKA Moscow (RUS): 1 (Sergei Ignashevich (PEN) 76')
Philips Stadion, Eindhoven, Holland - 34,000
Group C
Galatasaray (TUR): 1 (Selcuk Inan 64')
Astana (KAZ): 1 (Patrick Twumsai 62')
Turk Telekom Arena, Istanbul, Turkey - 26,464
Benfica (POR): 1 (Kostas Mitroglou 75')
Atletico Madrid (SPN): 2 (Saul Niguez 33', Luciano Vietto 55')
Estadio da Luz, Lisbon, Portugal - 47,630
Group D
Manchester City (ENG): 4 (David Silva 16', Raheem Sterling 79'/81', Wilfried Bony 85')
Borussia Monchengladbach (GER): 2 (Julian Korb 19', Raffael 42')
Etihad Stadium, Manchester, England - 41,829
Sevilla (SPN): 1 (Fernando Llorente 65')
Juventus (ITA): 0
Ramon Sanchez Pizjuan, Seville, Spain - 35,583
