Manchester United were dumped out of the Champions League after a dramatic 3-2 defeat at Wolfsburg saw them finish third in Group B.
United actually made the perfect start in Germany, as Anthony Martial slotted home a neat pass from Juan Mata, but the lead only lasted three minutes, as Naldo volleyed home a free-kick to level things up.
On the half hour mark, the Red Devils fell behind to a Vieirinha finish following a well worked passing move to put Louis van Gaal’s side in real trouble.
Despite falling behind, United, who were last knocked out at this stage in 2011, were still set to advance as PSV fell behind at home to CSKA, thanks to Sergei Ignashevich’s 76th minute penalty.
Just two minutes later, Luuk de Jong equalised for the Dutch side meaning United needed to find a goal at the Volkswagen Arena, and the three-time winners managed to do just that, as Josuha Guilavogui put the ball into his own net on 82 minutes.
However, just when the Premier League side thought they’d survived, Naldo headed home his second of the match, while PSV’s Davy Propper struck a winner in Eindhoven to break United hearts.
Van Gaal’s side will now enter the last-32 of the Europa League in February.
There was better news for the other half of Manchester though, as City topped their group for the first time following a 4-2 victory over Borussia Monchengladbach.
A fine move was finished off emphatically by David Silva to give Manuel Pellegrini’s side an early lead.
The Germans hit back though, taking the lead through goals from Julian Korb and Raffael as the Citizens found themselves 2-1 down at the break.
However, as it looked like they were about to finish second in Group D, two goals in two minutes from Raheem Sterling on his 21st birthday, and one from Wilfried Bony, saw the hosts turn the game on its head in the last 10 minutes.
And even better news was taking place in Spain, as City were able to claim top spot courtesy of Juventus’ 1-0 defeat to Sevilla.
Fernando Llorente came back to haunt his former club with the decisive header in the second half, meaning the Spaniards will be able to compete for a third consecutive Europa League title.
In Group A, Real Madrid silenced their critics with an emphatic 8-0 drubbing of Malmo.
Karim Benzema put aside pending legal worries with a hat-trick, but Cristiano Ronaldo went one better with four of his own, taking his tally in 11 in the group stage – a Champions League record.
Mateo Kovacic bagged his first for the club, as Rafael Benitez claimed his second ever 8-0 win in the competition following Liverpool’s thrashing of Besiktas in 2007.
PSG, who qualified in second, managed a 2-0 win at home to Shakhtar Donetsk.
Second half strikes from Lucas Moura and Zlatan Ibrahimovic sent Laurent Blanc’s men on their way, whilst their Ukrainian opponents now drop into the Europa League.
Atletico Madrid grabbed top spot in Group C with a fine 2-1 win at Benfica, who qualify in second spot.
Saul Niguez and Luciano Vietto put the Spaniards two up, before on-loan Fulham striker Kostas Mitroglou pulled one back for the hosts.
Kazakhstani champions Astana recorded a famous 1-1 draw at Galatasaray, but it wasn’t enough to stop the Turkish outfit booking their place in the Europa League.
Patrick Twusami gave the away side a shock lead just after an hour, but they were pegged back by a Selcuk Inan volley.
Player of the Night: Cristiano Ronaldo (Real Madrid)
Team of the Night: Real Madrid
Goal of the Night: Davy Propper (PSV EINDHOVEN vs CSKA Moscow)