ADVERTISEMENT
Real Madrid advanced to the Champions League knockout phase and Manchester City's campaign ended in the group stage for the second successive season after the Spanish and English champions drew 1-1 on Wednesday.
City needed a win to keep its hopes alive going into the Group D finale, 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 after fouling Sergio Aguero and the Argentina striker subsequently equalized from the penalty spot.
But Madrid held on for the draw to qualify with Borussia Dortmund, leaving City stranded at the bottom with just three points from five matches.
City's start belied the magnitude of the match for manager Roberto Mancini, whose expensively assembled side has been humbled in both of its appearances in Europe's elite competition.
And the Premier League leaders were made to pay after just 10 minutes when Angel Di Maria crossed from the right and Maicon failed to stop Benzema casually turning the ball in at the near post.
City was being tormented by Cristiano Ronaldo on his first appearance in the northern English city since leaving Manchester United three years ago.
The Portugal winger evaded Maicon and Pablo Zabaleta on the left flank before setting up Sami Khedira, who struck wide.
Ronaldo went close himself when he broke forward, and chipped the ball over Joe Hart after the City goalkeeper raced out to the edge of the area, but Zabaleta charged back and hacked the ball off the line.
It took around 20 minutes for City to put Jose Mourinho's side under any meaningful pressure, and when they did it took a fine save by Iker Casillas, who tipped over Aguero's shot.
There was also a break forward from Maicon, who had neglected his defensive duties but nearly made amends, playing a one-two with Aguero before striking wide.
City was also more assertive after the break, causing more trouble for the visitors.
Aguero looked most likely to grab the equalizer, with Maicon presenting him with a chance early in the second half that went wide.
City's attacking options were bolstered when Carlos Tevez replaced Samir Nasri on the hour.
But it was Aguero who came close again four minutes later.
After connecting with Maicon's cross from the right at the far post the net was at his mercy but Casillas managed to thwart the striker.
In the end, Aguero scored from the spot after Arbeloa was shown a second yellow card for bringing him down in the penalty area, giving City a lifeline.
But only a win would keep City alive in the Champions League, and the winner never came.
AMSTERDAM, Netherlands — Mario Goetze was involved in all four goals, including two by Robert Lewandowski, as Borussia Dortmund cruised into the knockout stage by outclassing Ajax.
Dortmund sealed the win before halftime at Amsterdam Arena thanks to its clinical finishing on the break and Goetze's skill and vision.
The 20-year-old Germany forward set up Marco Reus for the opener, scored the second, while his 41st-minute shot was blocked by goalkeeper Kennneth Vermeer with Lewandowski gratefully snapping up the rebound.
"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.
Shortly before being substituted, Goetze crossed from the left in the 67th minute to Lewandowski, who controlled the ball and shot past Vermeer from a tight angle for his fourth goal of this Champions League campaign.
"We saw amazing effectiveness today," said Ajax coach Frank de Boer. "But we gave away goals far too easily."
One of the only involvements from Goetze that didn't pay off came when he was booked for a dive in the penalty area in the 53rd minute.
Ajax brought on Lasse Schone in the second half for more creativity in midfield, and the team carved out more chances as Dortmund relaxed without being able to find the net due to goalkeeper Roman Weidenfeller saving shots from Christian Eriksen and substitute Viktor Fischer.
Substitute Daniel Hoesen finally grabbed a late consolation goal for four-time European champion Ajax with a deflected shot that lobbed over Weidenfeller.
Dortmund, the 1997 Champions League winner, started the match unbeaten in Group D, including a win and a draw against Real Madrid, a draw with Manchester City and a late 1-0 victory over Ajax at home.
Ajax travels to Madrid for its last match, while Dortmund faces Manchester City.
PORTO, Portugal — FC Porto set up a decider with Paris Saint-Germain in two weeks' time for the top spot in Group A.
Group leader Porto, undefeated so far, has 13 points to 12 for the second-place French club. They meet in Paris for the last group game on Dec. 4 to determine the top-seeded team in the draw for the tournament's knockout stage.
Lucho Gonzalez, unmarked in the Dinamo area, hit a left-foot shot for his second goal in the tournament after 20 minutes. Portugal's Joao Moutinho fired in a 67th-minute free kick, and Silvestre Varela sealed the victory five minutes from the end.
Porto, a two-time European champion which hasn't missed the knockout round since the 2005-06 season, was untroubled in a mostly uneventful encounter with Dinamo, which extended its winless streak in the tournament to 11 games.
Dinamo, looking for its first goal and first points in the tournament this season, almost scored with the first shot of the game as Sammir's 13th-minute effort bounced back off Helton's far post. Just before halftime Ivan Peko and Domagoj Vida also came close.
But Porto was always the likely winner and in the final stages Dinamo goalkeeper Ivan Kevala prevented a bigger loss by denying Varela and Jackson Martinez.
KIEV, Ukraine — Ezequiel Lavezzi scored both goals as Paris Saint-Germain secured a spot in the Champions League knockout stages.
The Argentine struck in the closing minute of the first half with a lob from the right side and an assist from Zlatan Ibrahimovic. Seven minutes into the second half, Lavezzi was alert to convert a quick pass in the box for his second strike after defender Yevhen Khacheridi's back pass to the goalkeeper rolled short.
Early on Dynamo often won the exchanges and put PSG under pressure in all four corners of the pitch. Before eventually taking control, PSG responded by trying to outmuscle Dynamo, which landed the French side with three yellow cards in a seven-minute span of the first half.
Dynamo's chances came mostly in the half.
After Miguel Veloso's free kick went wide in the 21st minute, he forced PSG goalkeeper Salvatore Sirigu to dive to deflect another attempt a minute later.
Sirigu couldn't control a header in the 25th and the rebound fell kindly for Denys Garmash, who's rushed shot from close range sailed over the crossbar.
By the 70th, Dynamo's chances went from set-pieces to relying on long-range efforts with a fall-off in continuity. PSG overcame its slow start and started looking more dangerous, bolstered by its two goals.
Still, Dynamo dominated ball control and had nine attempts on target to PSG's three.
LONDON — Jack Wilshere's first goal in two years and a sumptuous volley by Lukas Podolski earned Arsenal a win, clinching the English team's passage to the knockout stage for the 13th straight year.
After a poor first half, Wilshere brought Emirates Stadium to life in the 49th minute by flicking home a deft finish from Olivier Giroud's nod-down.
Podolski gave winless Montpellier too much to do by rifling in a sensational 63rd-minute volley after exchanging a one-two with Giroud, a former player of the French team.
Assured of a top-two finish, Arsenal will go into its last Group B game — at Olympiakos — a point behind leader Schalke.
With one game remaining, Schalke has 11 points and Arsenal 10. Olympiakos is four further back and the French side is bottom with one.
Podolski's strike was good enough to grace any occasion, the Germany forward meeting Giroud's floated pass with a powerful strike that flew past goalkeeper Geoffrey Jourdren from the edge of the area.
But it will be Wilshere's goal — his first since a 4-2 victory over Aston Villa in the English Premier League in November 2010 — that will arguably delight Arsenal fans more.
The young England midfielder has recently returned from a long spell out with myriad injuries and is seen as vital to Arsenal's chances of winning a first piece of silverware since 2005.
He starred here with his drive and energy, and his well-taken goal capped an impressive display in which he played 90 minutes for the first time since his long-awaited comeback.
Arsenal's record in the Champions League — advancing from the group every year since 2000 — is something Wenger uses against critics who slate him for the team's lack of trophies.
The Frenchman's side has maintained that record, adding to the confidence that had been boosted by a 5-2 win over Tottenham in the north London derby in the Premier League on Saturday.
The Gunners were slow to get going against Montpellier, Laurent Koscielny powering a header against the bar in the 11th minute and Podolski dragging a low shot wide with their best chances.
The cutting edge came in the second half, allowing Arsenal a stroll to the final whistle.
GELSENKIRCHEN, Germany — Schalke left it late to secure a 1-0 win over Olympiakos on Wednesday to qualify for the last 16.
Christian Fuchs settled the issue with 13 minutes remaining when he looked up and let fly from 35 metres to steer the ball inside the post. It was the Austrian defender's first Champions League goal.
Julian Draxler could have made sure of the win shortly afterward only to be denied by Olympiakos' Northern Irish goalkeeper, Roy Carroll.
Schalke had 25 attempts on goal, compared to the visitors' six.
ST. PETERSBURG, Russia — Zenit St. Petersburg came from 2-0 behind to draw with Malaga 2-2 in the Champions League on Wednesday.
Malaga qualified for the last 16 in its first Champions League campaign two weeks ago, while Zenit's hopes in Group C went in vain, as they depended on AC Milan not winning the late match against Anderlecht.
Diego Buonanotte opened the scoring for Malaga on the visitor's first attack in the eighth minute. A minute later, Roque Santa Cruz stole the ball from goalkeeper Vyacheslav Malafeev and passed it to Seba, who stunned Zenit by hammering the ball into an empty net.
Zenit was close to scoring in the half. Hulk curled a neat free kick over the wall of defenders only to shave the right post in the 15th. Eight minutes later, the Brazilian put Alexander Kerzhakov through into the box but the striker hit the outer side of the net.
Hulk then hit the crossbar in the 24th.
"We started really bad and were 2-0 down after 10 minutes," Danny said. "We had chances in the first half and could have scored the third goal in the second. It will be tough, but we still have chances to stay in Europe."
Zenit was more aggressive in the beginning of the second half and Danny finally scored from close range to narrow the gap in the 49th.
Three minutes later, Kerzhakov broke into the box but failed to hit an empty net over goalkeeper Willy.
The striker was also too late connecting to a cutting cross into the box from Axel Witsel in the 72nd.
Danny was close to an equalizer in the 86th but failed to control the ball in a goalmouth scramble and stood inside the net when Viktor Fayzulin blocked the clearance and curled the ball back into the right corner of the net to level.
BRUSSELS, Belgium — Stephan El Shaarawy and Philippe Mexes produced flashes of brilliance to lead AC Milan to a victory and a place in the next round.
The 20-year-old El Shaarawy won space in the penalty area in the 47th minute and deftly controlled a long cross with his left foot to set up right-footed curling shot that gave goalkeeper Silvio Proto no chance.
Mexes did even better in the 71st. Receiving a free kick on the edge of the box with his back to goal, his spectacular overhead bicycle kick dipped over Proto's head and into the far corner from 20 metres out.
Although Milan had dominated the first half, El Shaarawy's moment of class added to the momentum and the visitors grew in confidence after Anderlecht defender Bram Nuytinck was sent off for a foul on Alexandre Pato in the 70th minute.
The consolation goal of Tom De Sutter in the 77th had little impact.
El Shaarawy added an assist to his goal when he set up Pato for a third in injury time.
With one game remaining, Malaga has 11 points, three more than Milan. Anderlecht and Zenit St. Petersburg both have four points and are competing for a Europa League berth.
The victory was the result Milan coach Massimiliano Allegri craved with his team struggling in the first half of the season, having made its worst Serie A start in 71 years.
In Brussels, though, it showed off a newfound confidence — and an emerging star in El Shaarawy. The Italy international's fine strike brought up his 15th goal of the season in all competitions.
Since Milan is trailing in 12th position in Serie A, 17 points behind defending champion Juventus, the Champions League looks like the only competition in which the club can make its mark.
Milan was without captain Massimo Ambrosini, who had not recovered from the flu.
