Manchester United laboured to a 0-0 draw at home to PSV Eindhoven, as a place in the last-16 hangs in the balance.
It was a game with chances at a premium as the Red Devils were booed off by the Old Trafford faithful, and need to match the Dutch side’s result in the final match in order to qualify.
But Louis van Gaal’s side face a tricky trip to Wolfsburg, whilst PSV host CSKA Moscow, who sit bottom of the group and have yet to collect a point away from home.
In the other match, an Andre Schurrle double sent Wolfsburg to the top of Group B as they defeated CSKA 2-0 in Russia.
The former Chelsea winger opened proceedings with a low strike from just inside the box; goalkeeper Igor Akinfeev failing to keep it from squirming under his body.
Schurrle then added a second when he drilled home a neat half-volley from close range to eliminate Moscow.
The Bundesliga side need a point against United in their last match to seal their progress.
The other Manchester club also suffered a disappointing night as City fell to a 1-0 defeat at Juventus.
The Old Lady, who moved to the top of the group and sealed their spot in the last-16, stole the points early on when Mario Mandzukic was cleared of fouling Nicolas Otamendi, allowing him to volley Alex Sandro’s cross past Joe Hart.
Manuel Pellegrini’s side had already qualified for the knockout stage but were hoping to stay top to avoid some of the competition’s elite clubs in the next round.
In Germany, Borussia Monchengladbach are in pole position to claim the Europa League spot in City’s group as they defeated Sevilla 4-2.
Die Fohlen struck the first blow as Granit Xhaka’s speculative long range effort looked set to sail wide, but Lars Stindl popped up at the far post to tap Monchengladbach in front.
Second half strikes from Fabian Johnson and Raffael put the hosts 3-0 up, before Vitolo’s effort was quickly matched by Stindl’s second of the night.
Ever Banega’s late penalty restored some pride for Los Rojiblancos, but the Spaniards look as though they may not even get to defend the Europa League trophy they lifted in 2014 and 2015.
Real Madrid nearly blew a four-goal advantage but hung on to claim a much-needed 4-3 win for Rafa Benitez away at Shakhtar Donetsk.
Cristiano Ronaldo put in a match winning performance with two goals – his 83rd and 84th Champions League strikes in 120 matches -and two assists for Luka Modric and Dani Carvajal.
But despite a late double from Alex Teixeira and one from Dentinho giving the Spaniards a late scare, the 10-time winners secured the three points which sees them progress as Group A winners.
Zlatan Ibrahimovic’s return to Malmo was a successful one as his Paris Saint-Germain side thrashed Malmo 5-0 to qualify for the last-16.
Youngster Adrien Rabiot nodded the French outfit ahead with just three minutes gone, and Angel Di Maria doubled that lead soon after.
The talismanic Swede got in on the action himself in the second half, drifting in from the left and bending his attempt into the far corner.
Marcus Rosenberg’s penalty for the hosts then hit the upright, before Di Maria and Lucas Moura sealed an emphatic win for Laurent Blanc’s side.
Atletico Madrid also booked their place in the last-16 and moved top of Group C with a 2-0 win at home to Galatasaray.
French forward Antoine Griezmann popped up with a header to put Atleti in front, and later poked home a low cross from within the six-yard box.
Diego Simeone’s men leapfrogged Benfica after they drew 2-2 away to Astana.
The champions of Kazakhstan were denied their first ever Champions League following a comeback from a resilient Portuguese side.
First half strikes from Patrick Twumasi and Marin Anicic gave the hosts a shock 2-0 lead, but a Raul Jimenez brace either side of half time secured the Eagles the point needed to advance to the next stage.
Last-16 teams: Atletico Madrid, Barcelona, Bayern Munich, Benfica, Juventus, Man City, PSG, Real Madrid, Zenit
Eliminated: Astana, CSKA Moscow, Galatasaray, Malmo, Borussia Monchengladbach, Sevilla, Shakhtar Donetsk,
Player of the Night: Cristiano Ronaldo (Real Madrid)
Team of the Night: Paris Saint-Germain
Goal of the Night: Dani Carvajal (Real Madrid)