Madrid, AC Milan into last 16 of Champions League
FRANKFURT, Germany (AP) -Real Madrid and AC Milan, with 16 Champions League titles between them, advanced to the knockout stage of Europe's top club competition on Wednesday, along with Borussia Dortmund and Schalke to make it three out of three teams from Germany.
Nine-time champion Madrid held on for a 1-1 draw at Manchester City with 10 men, eliminating the Premier League champions in the process. Also in Group D, Dortmund beat Ajax 4-1 to go through as the top team.
Seven-time winner Milan won 3-1 at 10-man Anderlecht and Malaga drew 2-2 at Zenit St. Petersburg for both teams to advance from Group C.
Schalke defeated Olympiakos 1-0 and Arsenal beat Montpellier 2-0 to progress out of Group B.
Paris Saint-Germain won 2-0 at Dynamo Kiev to go through from Group A with FC Porto, which beat Dinamo Zagreb 3-0.
On Tuesday, Bayern Munich, Barcelona, Shakhtar Donetsk and Valencia also reached the knockout stage, while Chelsea is on the verge of becoming the first titleholder to fail to make it out of the group stage.
Chelsea's 3-0 loss at Juventus cost Roberto Di Matteo his job as coach despite leading the London club to the title in May. Rafa Benitez was later brought in to replace him in an interim role.
The goal of the day belonged to Milan defender Philippe Mexes against Anderlecht.
Receiving a free kick outside the box with his back to goal, Mexes sent a spectacular overhead kick from 20 meters out that dipped over goalkeeper Silvio Proto and into the far corner.
The goal resembled the fourth strike by Zlatan Ibrahimovic against England last week. Ibrahimovic failed to score Wednesday, but Ezequiel Lavezzi scored a double as Paris Saint-Germain cruised in Kiev.
Germany forward Lukas Podolski found the net with a spectacular volley in Arsenal's win over Montelliper that also featured Jack Wilshere's first goal in two years. Then Gunners advanced from group stage for the 13th straight year.
Podolski met Olivier Giroud's floated pass with a powerful first-time strike that flew past goalkeeper Geoffrey Jourdren from the edge of the area in the 63rd.
After a poor first half, Wilshere brought Emirates Stadium to life in the 49th minute by flicking home a deft finish from Giroud's nod-down.
Assured of a top-two finish, Arsenal will go into its last Group B game at Olympiakos a point behind Schalke. Both sides will want to finish top to secure what would likely be an easier last-16 match.
Manchester City's campaign ended in the group stage for the second successive season after the Spanish and English champions drew 1-1.
City needed a win to keep its hopes alive, but Karim Benzema exploited sloppy defending to put Madrid ahead after just 10 minutes at Etihad Stadium.
City secured a lifeline in the 74th when Alvaro Arbeloa was sent off for fouling Sergio Aguero, who subsequently equalized from the penalty spot. But Madrid held on to qualify with Borussia Dortmund, leaving City stranded at the bottom with just three points from five matches.
Young Italy forward Stephan El Shaarawy scored one goal and set up Alexandre Pato in injury time as Milan completed its win over Anderlecht. Milan is struggling in the Italian league but is compensating for that in the top competition for European clubs.
The consolation goal of Tom De Sutter in the 77th had little impact. Bram Nuytinck was sent off for a foul on Pato in the 70th minute.
Dortmund, which failed to advance from the group stage last season, extended its impressive run, with Germany midfielder Mario Goetze involved in all four goals, including two by Robert Lewandowski.
Dortmund, the 1997 champion, sealed the win before halftime at Amsterdam Arena thanks to its clinical finishing on the break and Goetze's skill and vision.
Marco Reus added another goal for the German champion.
"In the first half they were only in front of goal three times and they scored three goals. They were so effective,'' said Ajax captain Siem de Jong.
Substitute Daniel Hoesen finally grabbed a late consolation goal for four-time European champion Ajax with a deflected shot.
Schalke left it late to secure its win, with defender Christian Fuchs driving home from long range with 13 minutes remaining.