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Manchester United's 23-match unbeaten home record in the Champions League stretching back to 2005 was ended by Besiktas who won 1-0 at Old Trafford on Wednesday.
Rodrigo Tello netted the only goal for the Turkish side after 20 minutes with a shot from distance.
United, who had already qualified for the last 16, piled forward in search of an equaliser and were denied late in the game by some fine saves from keeper Rustu Recber.
AC Milan were the last side to win at Old Trafford in the competition when they won 1-0 in the first knockout round in February 2005.
Besiktas, already out of contention for the knockout phase, came within a whisker of making it 2-0 in the 41st minute when a low shot by Michael Fink scraped past keeper Ben Foster's left upright but just on the wrong side of the post.
United require one more point from their remaining fixture to finish top of Group B.
They fielded a number of less familiar faces in their lineup with Gary Neville, Anderson, Ji-Sung Park, Wes Brown and Nemanja Vidic bolstering an otherwise inexperienced side.
Midfielder Gabriel Obertan and striker Daniel Welbeck played well in the first half but were given little support from the rest of the team and not even the late introduction of veteran striker Michael Owen could save United from their fate.
Besiktas were roared on by a small band of noisy supporters who largely overshadowed the majority of the 74,242 home fans with constant chanting throughout the match.
Nicolas Anelka's second-half header earned Chelsea a 1-0 win against Porto on Wednesday and guaranteed the English side will win Champions League Group D with one match still remaining.
The goal came from a simple move in the 69th minute. With the Porto defenders static, Yuri Zhirkov fed Florent Malouda on the left wing and the Frenchman crossed for his compatriot Anelka to head in unchallenged.
"It's not easy winning at this stadium, but we did it. In the first half we ran some risks and weren't very well, but I think we had a good game, though not fantastic," Chelsea coach Carlo Ancelotti said.
"It was a very important win because it allows us to now concentrate on the Premier League," he added.
Anelka was a threat throughout and created the first chance on 15 minutes with a powerful shot that keeper Beto blocked with some difficulty.
Porto, who like Chelsea had already qualified for the last 16, responded with Argentine midfielder Fernando Belluschi forcing a save from Petr Cech. Striker Radamel Falcao pounced on the rebound but also sent his shot straight at the keeper.
The influential Belluschi had the best chance of a mostly tame first half on 29 minutes, sending a shot crashing against Cech's bar.
The Premier League leaders showed more intent at the start of the second half and playmaker Deco almost netted against his former club on 52 minutes, collecting Rolando's flawed clearance but shooting just wide.
Porto drove forward in search of an equaliser, but substitute forwards Hulk and Ernesto Farias were unable to trouble a composed Chelsea backline.
"No one can forget that we played against a great team, in my opinion the best in English football, with great quality players who always remain serene," Porto coach Jesualdo Ferreira said.
"Porto could have perfectly well drawn this match. Even before Chelsea scored we could have had the first goal, but its the three points that count in the end."
Chelsea have 13 points from five matches with Porto on nine. Atletico Madrid have three and APOEL Nicosia have two.
Gonzalo Higuain scored the only goal for Real Madrid in a dull 1-0 win over FC Zurich that sent his team to the top of Champions League Group C on Wednesday.
The Argentine striker was played through by Kaka to score after 21 minutes but despite their dominance Real struggled to add to their lead and they were whistled off by the Bernabeu at the end.
The biggest cheer of the night came when Cristiano Ronaldo replaced Raul midway through the second half, returning to action after two months out with an ankle injury.
Zurich did not manage to seriously trouble Real goalkeeper Iker Casillas.
The win put Real on 10 points, two ahead of AC Milan who drew with Olympique Marseille, with one round of group matches left.
"I am concerned with the quality of our play. I don't like this type of football and it's not style of play I want from the team," Real coach Manuel Pellegrini said.
"We just lacked the second goal which would have settled us and allowed us to open up. With only a one goal advantage the game was tightly balanced. The important thing was the win today."
Real camped on the edge of the Zurich area and it was Kaka who prised open their massed ranks.
The Brazilian, who had already had a long-range effort saved, danced past two players before slipping the ball into the area for Higuain and the Argentine beat Johnny Leoni with a low shot.
SUPERB VOLLEY
Xabi Alonso stung Leoni's hands with fierce drive and Marcelo cracked a superb volley against the post at a corner, but there was little else to cheer a chilly stadium.
The appearance of Ronaldo to warm up just after the break brought the home fans to life briefly, and he was roared on to to the pitch after 67 minutes.
But the Portugal forward failed to lift the team.
In the closing stages substitute Rafael van der Vaart was played through on goal but blasted over the bar with only the keeper to beat, and Leoni saved one-handed from Ronaldo after a surge into the area.
Zurich coach Bernard Challandes said: "Bearing in mind the last few weeks where we have not been doing so well in the league at home we are relatively pleased.
"We were up against the richest team in the world and we weren't humiliated. Our confidence wasn't high and it's an acceptable result for us."
AC Milan and Marseille must wait until the final round of matches to see who reaches the Champions League knockout stages after the sides drew 1-1 at the San Siro on Wednesday.
The Serie A outfit are a point above Didier Deschamps' team in Group C and a win at FC Zurich next month would put them through, leaving Marseille to battle leaders Real Madrid in southern France for the other qualification spot.
The hosts, who won 2-1 in Marseille in the opening group match, went ahead on 10 minutes when striker Marco Borriello ambled past centre back Gabriel Heinze in the box and calmly finished.
The lead did not last long however, with Milan's defence looking as shaky as Marseille's backline.
The French side's captain Mamadou Niang cruised past fullback Massimo Oddo on 16 minutes and his cross was palmed by Dida straight to Lucho Gonzalez, who could not miss from 10 metres out.
Injury-prone Borriello, who shrugged off another knock to start instead of Filippo Inzaghi, could have grabbed a second but for a superb last-ditch tackle from Souleymane Diawara.
Brazilian Alexandre Pato also lobbed just over for Milan but the visitors were always in the hunt and Fabrice Abriel missed by a whisker with a fierce drive from distance.
Marseille had the better of the second half with forward Brandao spurning the best chance when he clipped the bar from close in after Niang's cross.
Diawara then headed against the post late on as Milan tired badly but coach Leonardo opted against bringing on experienced goal poacher Inzaghi or other fresh legs.
The home side, who beat Cagliari 4-3 at the weekend, did come close through Borriello's header in the closing stages and had earlier been denied a penalty when Gianluca Zambrotta was booked for diving in the box after nice work by Ronaldinho.
Bayern Munich, facing an early Champions League exit, revived their chances of reaching the last 16 on Wednesday as they beat Maccabi Haifa 1-0 and rivals Juventus lost at Girondins Bordeaux.
AC Milan missed a chance to qualify when they were held 1-1 at home by Olympique Marseille and Real Madrid produced an uninspiring 1-0 win over Swiss champions FC Zurich in the same group.
Croatia's Ivica Olic tapped in the winner from a rebound in the 62nd minute for Bayern, their only goal in three home games in Group A.
Bayern stayed third with seven points but moved within one of Juventus, who lost 2-0 at already-qualified Bordeaux where Fernando and Marouane Chamakh scored in the second half.
The Bavarians must win away to Juventus in their final game to qualify at the Italians' expense.
Gonzalo Higuain scored to send Real top of Group C with 10 points, two ahead of Milan with Marseille a further point behind.
German champions VfL Wolfsburg missed a chance to book their place when they lost 2-1 at CSKA Moscow, who revived their own hopes in Group B.
Manchester United, already through to the second round, lost a 23-match unbeaten home record in the tournament as they were beaten 1-0 by Turkey's Besiktas at Old Trafford in the same group.
Two second-half headers helped Girondins Bordeaux retain top spot in Champions League Group A with a 2-0 home win over Juventus on Wednesday.
The French champions, who have already qualified for the knockout stage, now have 13 points, five ahead of second-placed Juve with a game to spare.
Juventus, who suffered their first defeat in the group stage this season, will join Bordeaux in the knockout phase if they do not lose at home to Bayern Munich in their next game.
Bordeaux snatched a fourth consecutive win in the Champions League through goals by midfielders Fernando and striker Marouane Chamakh.
The French champions got off to a better start despite playmaker Yoann Gourcuff's absence through injury and their passing game helped them dominate throughout the first half.
Their best chance came just before the interval when defender Matthieu Chalme set up Marouane Chamakh in the box but the Morocco striker's effort from close range was saved by Gianluigi Buffon.
Bordeaux eventually broke the deadlock nine minutes into the second half when midfielder Fernando headed in a Jaroslav Plasil free kick.
Fit-again Alessandro Del Piero made the starting line-up as a right winger but the Italian veteran failed to make an impact until he moved into a more central position in second half.
Del Piero created Juve's best chance before being substituted but Diego and Amauri both missed the ball at close range from one of his crosses.
Juventus tried to push harder to snatch a late equaliser but Chamakh sealed Bordeaux's win with a stoppage time header from a Wendel corner kick.
CSKA Moscow came from behind to beat VfL Wolfsburg 2-1 in their Champions League Group B match on Wednesday to keep alive their hopes of reaching the knockout round.
Edin Dzeko had put the German champions ahead against the run of play midway through the first half before Czech striker Tomas Necid and Serbian winger Milos Krasic struck eight minutes apart early in the second half to give the Russians the points.
The win moved CSKA level with second-placed Wolfsburg on seven points with the last round of matches to come.
But the Germans, who needed only a draw in Moscow to join English champions Manchester United in the last 16, still have the edge over CSKA after beating them 3-1 in the first game.
CSKA coach Leonid Slutsky had mixed feelings about the outcome. "I'm satisfied with the win but a little disappointed because I was hoping for a bigger victory," he told Russian television NTV.
"Still, the whole team showed a lot of courage to pull off this win after falling behind early in the game."
Obafemi Martins sent Dzeko through and the Bosnian striker beat the offside trap to shoot past CSKA keeper Igor Akinfeyev from close range in the 19th minute.
SPEEDY KRASIC
Krasic could have levelled just a few minutes later but missed the target after dribbling past several Wolfsburg defenders.
CSKA defender Alexei Berezutsky then wasted another great chance, shooting straight at Wolfsburg keeper Diego Benaglio from six metres following a corner. Benaglio also made a fine save to deny Pavel Mamayev early in the second half.
Necid finally beat Benaglio with a powerful header from close range in the 58th minute after pin-point cross from Yevgeny Aldonin.
Krasic, who tormented the German defence with great solo runs on the artificial Luzhniki turf throughout the game, then fired the hosts ahead with a 30-metre blast into the top corner.
At the other end, Dzeko had the ball in the CSKA goal for a second time shortly after the re-start but this time he was ruled offside.
Wolfsburg, who were missing their top scorer Brazilian Grafite through suspension, pressed forward late in the game and Marcel Schaefer came close with an equaliser only for Akinfeyev to push the ball over the bar and preserve the win.
In the final group games on Dec. 9, Wolfsburg host Manchester United, who have already qualified, while CSKA travel to Istanbul to play Besiktas.