English champions Manchester City are out of the Champions League, after drawing 1-1 with Real Madrid in Group D.
The Spanish champions made a far brighter start than the home side and took the lead in the 10th minute.
Argentinian winger Angel Di Maria crossed to the far post for French striker Karim Benzema to score from close-range.
Real had numerous chances to extend their lead in the first half, but failed and went in at the break one goal up.
City came out much stronger in the second half. However the equaliser didn’t come until the 75th minute. Sergio Aguero went down in the area under a challenge from Alvaro Arbeloa and the referee pointed to the spot.
The former-Liverpool full-back was shown a second yellow card and dismissed. Aguero made no mistake from the spot with the resulting spot-kick. City pushed for a winner, but the Spanish champions held on to the draw. The result means that City are now out of the competition.
Elsewhere in Group D, Dortmund hammered Ajax 4-1 in the Amsterdam Arena. Dortmund opened the scoring on eight minutes through exciting young attacking midfielder Marco Reus. Mario Gotze and Robert Lewandowski made it three for the German champions before the interval.
Lewandowski added a second goal in the second half and Danny Hoesen scored a consolation goal for the home side. The victory means that Dortmund and Real Madrid have both qualified for the knockout stages.
Meanwhile Manchester City and Ajax will battle it out for third place, which would mean the consolation prize of a place in the Europa League.
Arsenal have qualified for the last 16 of the competition after beating Montpellier 2-0 at the Emirates Stadium. The first half was a scrappy affair with no flow to it; both Arsenal goals came in the second period.
Jack Wilshere clipped home the opener on 49 minutes from an Oliver Giroud knockdown, before German international Lukas Podolski fired home a superb volley in the 63rd minute. The victory means that the Gunners will now fight it out with German side Schalke for top spot in the group.
The side from Gelsenkirchen defeated Olympiakos 1-0 at the Veltins Arena. The only goal of the game came from a superb 77th minute strike from Christian Fuchs. The win leaves Schalke ahead of the Gunners by one point.
Zenit and Malaga drew 2-2 in Group C, as the Spanish side qualified for the knockout stages as group winners. The La Liga side were two goals up in just nine minutes, Argentinian midfielder Diego Buonanotte and Sebastian Fernandez scoring the goals.
The Russian champions fought back though and goals from Portuguese star Danny and midfielder Viktor Fayzulin were enough to earn their side a point. However the point wasn’t enough to keep them in the competition.
AC Milan have also qualified for the last 16 with a 3-1 win at Anderlecht. Milan took the lead through highly-rated youngster Stephen El Shaarawy. Milan’s second goal was an absolute stunning strike from centre-back Philippe Mexes, the French international scoring with a fantastic overhead kick.
Anderlecht substitute Tom de Sutter got a goal back for the home side. However in the dying moments of the game another substitute Alexandre Pato wrapped up maximum points for the visitors.
Anderlecht will now have to compete with Zenit for third spot and a place in the Europa League.
Group A saw big spending PSG win 2-0 at Dinamo Kiev and qualify for the last 16 in the process. Goals either side of half-time from Ezequiel Lavezzi were enough to clinch all three points in Ukraine.
Porto will be joining the French side in the knockout stages of the competition after beating Dinamo Zagreb 3-0. Argentinian midfielder Lucho Gonzalez opened the scoring after 20 minutes. Portuguese internationals Joao Moutinho and Silvestre Varela added goals in the second half.
Should Manchester City be doing better in the Champions League?