Dejected Manchester City players leave the field after drawing 1-1 with Madrid
Manchester City failed to reach the last 16 of the Champions League for the second successive season following a draw at home to Real Madrid, while Arsenal progressed after beating Montpellier.
City needed to win but were dealt an early blow when Karim Benzema converted Angel Di Maria's cross, reports the BBC.
Striker Sergio Aguero equalised from the spot after the break following a foul by Alvaro Arbeloa who was subsequently shown a second yellow.
Aguero had a close-range shot superbly blocked by keeper Iker Casillas.
Real secured their place in the knockout stage along with Borussia Dortmund, who defeated Ajax 4-1 to win Group D with one round of group matches remaining.
And at the Emirates, Arsenal reached the Champions League knockout stage for a 13th consecutive season as they outclassed Montpellier and Schalke beat Olympiakos.
The Gunners struggled for momentum in a disappointing first half that saw Laurent Koscielny head against the bar.
But they improved after the break and Jack Wilshere scored his first goal since returning from injury with a chipped finish from close range.
Lukas Podolski sealed the win with a stunning volley as Montpellier faded.
It was an unstoppable strike that will be replayed many times over - a fitting way to secure a place in the last 16.
Schalke's home victory over Olympiakos keeps the Germans top of Group B on 11 points, one clear of Arsenal with one game left.
Olympiakos, who host Arsenal on 4 December, are third on six points and will drop into the Europa League, while Montpellier remain bottom with just one point from five matches.
This was not a vintage win and Arsenal looked disjointed until breaking the deadlock, but they can be pleased with the result and will now attempt to finish above Schalke in top spot.
For a club competing in the Champions League for a 15th consecutive season, it was remarkable that Arsene Wenger's men had never previously beaten a French club at home in the competition.
Saturday's morale-boosting victory over Tottenham, coupled with Montpellier's domestic and European struggles this season, gave the Gunners hope of bucking that trend.
In other matches, Zenit drew 2-2 with Malaga, Borussia Dortmund hammered Ajax 4-1 in Holland, Anderlecht lost 1 – 3 to AC Milan, French side, PSG was too strong for Dynamo Kiev winning 2-0, FC Porto beat Dinamo 3-0 and Schalke 1-0.
Arsenal 2 - 0 Montpellier FT
Man City 1 - 1 Real Madrid FT
Zenit St P'sbg 2 - 2 Malaga FT
Ajax 1 - 4 Borussia Dortmund FT
Anderlecht 1 - 3 AC Milan FT
Dynamo Kiev 0 - 2 Paris SG FT
FC Porto 3 - 0 Din Zagreb FT
Schalke 04 1 - 0 Olympiakos