Real Madrid and Borussia Dortmund qualified for the Champions League knockout stages from the arguably toughest group on Wednesday, eliminating Manchester City and Ajax Amsterdam.

Ten-man Real were held 1-1 at City but that was good enough to advance along with Dortmund, who are assured of first place in group D from a 4-1 triumph at Ajax.

Arsenal, Paris St Germain, Schalke and AC Milan also advanced on the night, with Milan’s Philippe Mexes on target in a 3-1 win at Anderlecht with a bicycle kick from the edge of the area, which was almost as impressive as Zlatan Ibrahimovic’s for Sweden last week against England.

The six teams join Barcelona, Malaga, Valencia, Porto, Manchester United and Shakhtar Donetsk in the round of 16. The remaining four berths are decided in the final round of group action on December 4 and 5.

The record champions Real dominated at the Etihad and took the lead in the 10th minute when Benzema volley home a cross from Angel di Maria from point blank range.

City improved after the break with Sergio Aguero aiming at Iker Casillas from inside the goalmouth. Aguero levelled on a 73rd-minute penalty after being brought down by Alvaro Arbeloa who had to go for this second bookable offence, but the draw kept City winless and saw them eliminated in the group stage the second straight year.

Dortmund remained unbeaten with their emphatic win in Amsterdam.

Mario Goetze set up Marco Reus in the eighth, scored the second with a low shot in the 36th, was involved in the third from Lewandowski in the 41st and fed the Polish forward for the fourth in the 67th.

Daniel Hoesen scored late for Ajax.

Arsenal did better than City and beat group B bottom side Montpellier 2-0 from Jack Wilshere and a smashing volley by Lukas Podolski, both set up by Olivier Giroud.

Arsenal has 10 points, one point shy of Schalke, who edged Olympiakos Piraeus 1-0 from Christian Fuchs’ long-range shot. Piraeus will finish third on currently six points, Montpellier has one.

Forward Stephan El Shaarawy opened the scoring in the 47th and Mexes then chested a pass with his back to the goal and found the target with a great overhead kick for the second shortly after Bram Niytinck was sent off for the hosts.

Tom de Sutter revived Anderlecht’s hopes but Alexandre Pato wrapped up matters for Milan late in the game.

Milan has eight points to rank behind group winners Malaga (11), who blew a 2-0 lead from Diego Buonanotte and Seba in a 2-2 draw at Zenit St Petersburg. Danny and Viktor Fayzulin levelled for the hosts who had Vladimir Bystrov red-carded after the final whistle.

Zenit and Anderlecht have four points apiece.

PSG followed Porto into the round of 16 from group A, 2-0 at Dynamo Kiev from Ezequiel Lavezzi’s double. Porto won 3-0 against Dinamo Zagreb from Lucio Gonzalez, Joao Moutinho and Silvetstre Varela.

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