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Manchester United, Champions League finalists in three of the last four seasons, were knocked out of the group stage after a humbling 2-1 loss at FC Basel on Wednesday, one of their unhappiest nights in European competition.
Marco Streller and Alexander Frei, who both quit the Switzerland national team this year, scored early and late to take the Swiss champions beyond the group stage for the second time in four attempts.
Phil Jones scrambled a late goal for lacklustre United, for whom winger Nani carried the most attacking threat as striker Wayne Rooney had another frustrating evening.It was only the third time in 17 Champions League participations, all under manager Alex Ferguson, that United had failed to progress beyond the group stage.
While Basel and their boisterous fans celebrated as if they had won the competition itself, United were left to contemplate playing in the much-maligned Europa League.
Basel players mobbed coach Heiko Vogel, who had no experience as coach of a senior side when he took over in November following the departure of Thorsten Fink to Hamburg SV.
Basel, who had looked utterly out of their depth in a 2-0 home defeat by Benfica earlier in the group, snatched second place in Group C with 11 points, one behind the Portuguese side, while United were third with nine.
The visitors were left to rue their 3-3 draw at home to Basel when they squandered a 2-0 halftime lead.
"I'm very, very proud," Vogel said. "Tactically, mentally, physically it was extraordinary. I will leave the superlatives to you."
Ferguson admitted that the Europa League would be a new experience.
"It's a competition I've never been in with United, it means a lot of Sunday games, that's not ideal but that's our penalty for not qualifying tonight," he said.
"Of course, we're disappointed, there's no other way you can feel. We had so much possession up to the last third of the field. Some of our play up to that point was very good, you have to say our finishing let us down."
Needing only a draw to qualify, United were quickly in trouble when De Gea misjudged Xherdan Shaqiri's cross and prodded the ball with his foot straight to Streller who scored from close range despite mishitting his shot.
United still had plenty of time to put things right and dominated the game, although, with the impish Shaqiri in midfield, Basel were always dangerous in attack.
Rooney, who scored two goals in England's 3-1 win over Switzerland at the same stadium last year, nearly levelled with a shot on the turn from Ryan Giggs's pass which was well stopped by Yann Sommer.
He missed an outstanding chance just after the break when another Giggs pass sent him clear down the left but he shot wide of the far post.
Rooney, who has gone eight games without scoring, also headed over from close range from Chris Smalling's cross and curled another shot just wide from outside the area.
Nani's runs down the right were by far United's most dangerous weapon, although the nearest United came to an equaliser was when Basel defender Markus Steinhoefer crashed an attempted clearance against the underside of the bar.
Frei, Switzerland's record goalscorer who has spent a good part of his career at Basel, nearly added a second with a chipped free kick which was superbly turned over by De Gea.
The 32-year-old fittingly grabbed the decisive goal in the 84th minute, scoring at the far post after the United defence misjudged Shaqiri's inswinging cross.
Jones scrambled one back five minutes later but it was too late.Manchester City beat a weakened Bayern Munich side 2-0 on Wednesday but it was not enough to stop the Champions League debutants making a group-stage exit.
City, needing a win as well as Napoli to drop points at Villarreal in order to progress, went on the offensive from the start against the Group A winners but had to wait until the 36th minute for their opener.
It came with David Silva's low shot from 20 metres out after a neat flick by Edin Dzeko, who was the provider for their second, seven minutes after the restart, as his pass found a charging Yaya Toure who finished calmly.
City achieved their part of the equation that would take them through alongside Bayern but with Napoli winning 2-0 at Villarreal it was not enough for the English side, who now go through to the Europa League round of 32.
City manager Roberto Mancini showed his intention to attack by naming Samir Nasri, David Silva, Sergio Aguero and Edin Dzeko in the starting lineup and the quartet were involved in nearly every move forward.
The hosts had the ball in the back of the net in the 15th minute when Silva's free kick was headed in by Joleon Lescott but it was disallowed for a foul by the defender on Bayern keeper Joerg Butt.
Unperturbed, City continued to push forward with Dzeko heading wide a few minutes before he set up Silva nine minutes before the break.
They started the second half as they ended the first, doubling the score when Aguero played the ball through to Dzeko who had spotted Toure's perfectly timed run and the Ivorian slotted it past Butt.
Bayern, who named a team containing just three survivors from the one that started against City in their 2-0 win over the English club in Germany in September, lacked a cutting edge and aside from a couple of long-range shots offered little in reply.
Knowing that no matter how many goals their side scored, qualification was not in their hands, one of the most uttered questions among home fans throughout the game was "what's the score in the Napoli game".
The groans grew as news of the goals in Spain filtered through as City fans resigned themselves to watching the Premier League leaders compete in the second tier of European competition.
Bayern finish with 13 points from their six group games, with Napoli on 11, City on 10 and Villarreal on 0.Real Madrid secured a 3-0 win over Ajax Amsterdam on Wednesday, their sixth consecutive victory in Champions League Group D, to leave the Dutch club in misery as they missed qualification for the knock-out phase.
Ajax ended the night level on eight points with Olympique Lyon, 7-1 winners at Dinamo Zagreb, but were overtaken by the French side on goal difference.
Real opened the scoring after 14 minutes when a pass from Kaka beat the Amsterdam offside trap and put Jose Callejon in a scoring position.
Ajax, who needed only a draw and started with a seven goal advantage over Lyon, were unlucky when first half goals by Nicolas Lodeiro and Vurnon Anita were ruled offside.
Four minutes before the interval Real's Karim Benzema set up Gonzalo Higuain to double the lead and in the second half only Sulejmani came close to bringing his side back in the match when his curved shot hit the bar. Callejon made it 3-0 for Real in stoppage time.
"We were so close and if you go out like this it tastes bitter," Ajax coach Frank de Boer told NOS-TV.
"I noticed some tension in my team in the opening phase but after the opening goal we did well and scored two good goals which were wrongly disallowed.
"It should have been 2-2 at halftime as we were not worse than Real who didn't really play with everything they've got."
Vasily Berezutski scored a late winner as CSKA Moscow dramatically qualified for the knockout stages of the Champions League after defeating Group B winners Inter Milan 2-1 at the San Siro Wednesday.
Going into the match needing a win and the Lille-Trabzonspor match to end in a draw in order to qualify, the defender headed home with four minutes to go, seconds after Diego Milito had headed against the crossbar at the other end.
The Russian side took the lead five minutes after the break through Ivorian striker Seydou Doumbia, but dreams of progression appeared to have evaporated when Argentine midfielder Esteban Cambiasso equalised within a minute.
With Lille-Trabzonspor ending goalless, CSKA qualified in second place with eight points from six games, two points behind Inter. Trabzonspor go into the Europa League having finished third with French champions Lille bottom.
Champions League debutants Napoli held their nerve to beat Villarreal 2-0 with goals from Gokhan Inler and Marek Hamsik securing them a place in the last 16 at the expense of Manchester City on Wednesday.
The Italians finished second in Group A behind Bayern Munich, with the Germans falling 2-0 at third-placed City who needed to win and hope Napoli drew or lost.
Swiss midfielder Inler struck from 25 metres out in the 65th minute to settle his nervous team-mates who had struggled to make headway against already eliminated Villarreal.
Slovakian international Hamsik bundled the ball in from close range at a corner in the 76th, leaving their Spanish hosts, semi-finalists in 2006, without a point in their six group games.
"We are a well-rounded team and we have a lot of running in us. We like to get the ball and play football and this was key to us passing to the next stage," Napoli's Argentine forward Ezequiel Lavezzi told Spanish television.
"To be in a group as difficult as this makes it particularly sweet to progress. It might be historic for us but we want to go further.
"I wasn't interested in what Manchester City were doing during the game. We were determined to concentrate on what we were doing and winning our game, and luckily we achieved that," he said as a noisy contingent of travelling Italian supporters celebrated in the background.An early tap-in from Paraguay striker Oscar Cardozo earned Benfica a 1-0 home win over Romanian champions Otelul Galati on Wednesday which secured them top spot in Champions League Group C.
The Lisbon club ended the group phase above second-place Basel who shocked Premier League champions Manchester United with a 2-1 win in the final match.
"We must stress this brilliant campaign of ours," Benfica coach Jorge Jesus told reporters. "Benfica's group had three excellent teams and United, who were the favourites, were knocked out, that says it all."
Otelul exit the Champions League without earning a single point in their debut campaign.
Benfica had secured qualification with an impressive 2-2 draw at United in the previous round and allowed themselves to relax and control the tempo of the match after an early Cardozo goal.
Argentine winger Nicolas Gaitan ran to the byline inside Otelul's box and his clever pass found the Paraguayan striker who coolly tapped in the winner in the seventh minute.
Silky playmaker Pablo Aimar and the clever Axel Witsel pulled the strings in the midfield, giving the visitors little leeway as Benfica controlled possession throughout.
"We are very ambitious. We accomplished the objective of being first but the key goal was to get to the last 16 round. Now we will see what the draw has in stall for us and in what form we will be in the knockout," Aimar said.
Cardozo, Benfica's top goalscorer in the competition with three goals, almost grabbed a second in the 33rd minute with a shot from outside the box that went inches wide.Trabzonspor were denied a spot in the Champions League last 16 in their debut season after a battling 0-0 draw at Group B rivals Lille on Wednesday was rendered redundant by CSKA Moscow winning 2-1 at Inter Milan.
Going into the game, Lille knew only a win would do to secure qualification and Trabzonspor were seeking a victory while also being aware that a point would be enough if CSKA Moscow did not win at group winners Inter in the other match.
Hosts Lille came rapidly out of the traps with midfielder Eden Hazard having three good chances but the French champions wilted after the break against a dogged defense.
Trabzonspor, now bound for the Europa League, wrongly thought they were going through to the Champions League first knockout round even after a decisive late goal gave CSKA victory at Inter but the news eventually filtered through.
Lille boss Rudi Garcia made two defensive substitutions despite needing a victory, taking attacking midfielder Joe Cole off on 69 minutes and replacing a fullback with another as frustrated fans inside the Metropole shook their heads.
Ludovic Obraniak, who came on for Cole as his side slipped to bottom of the group, told reporters: "We did everything we could tonight. But it was not enough. We still have our national title to defend but we are all disappointed.
"The Champions League is a prestigious competition. We wanted to go through. It was just impossible tonight."
Olympique Lyon staged an astonishing fightback to earn a 7-1 win at 10-man Dinamo Zagreb in their Champions League Group D match Wednesday and reach the knockout stage of the competition.
The French side went through after Ajax Amsterdam, who started the night three points ahead of them with a vastly superior goal difference, were beaten 3-0 at home by group winners Real Madrid.
Lyon's challenge looked all but over when they fell behind to a Mateo Kovavic goal in the 40th minute, after Dinamo had their midfielder Jerko Leko sent off for a second bookable foul midway through the first half.
But the French side's striker Bafetimbi Gomis led their revival with four goals, with Maxime Gonalons, Lisandro Lopez and Jimmy Briand netting the other three to send them into the last 16 of Europe's premier club competition.
Gomis's first three goals in the space of seven minutes either side of halftime are a Champions League hat-trick record.