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Ezequiel Lavezzi and Edinson Cavani combined to spark Napoli's 3-1 comeback win over Chelsea in their Champions League last 16 first-leg match on Tuesday that deepened the gloom hanging over the London club.
The South American pair made the difference in a match where the visitors had taken the lead through Juan Mata before squandering two more chances and putting under-fire manager Andre Villas-Boas under yet more pressure.
Lavezzi scored Napoli's first and third goals, the first of the competition for the Argentine and both laid on by Cavani who notched the other himself. The prolific Uruguayan took his tally to six in the Champions League and 19 in his last seven outings.
Napoli's win left England in danger of missing out on the quarter-finals after Arsenal, the Premier League's only other team in the last 16, were thumped 4-0 at AC Milan last week.
It also left Villas-Boas facing more questions about his future as the poor run of form continued for the London team, who have won only two of their last 10 Premier League games and who drew against second tier opponents in the FA Cup last weekend.
Asked if he expected to be in charge by the time his side host Napoli for the return leg on March 14, the Portuguese told Sky Sports: "Yeah, for sure."
Chelsea's day had got off to a bad start with news that captain John Terry could be sidelined for several weeks after aggravating a knee injury and it soon got worse.
"After the first goal, we missed opportunities to go 2-0 up and then we should have defended better but we made a couple of mistakes against Napoli with their attack you are going to get punished," said Villas-Boas.
"I think the third goal was perfectly avoidable ... We can create problems with our attacking options and we created problems (for them) today.
"It is a game of efficiency and Napoli had it. I think the statistics are very similar for both teams. Both teams created a lot. The game was open," he added.
Napoli, unbeaten at home since returning to European competition in 2008 following a 13-year absence, were quickly on the attack and goalkeeper Petr Cech twice prevented Chelsea from shipping an early goal.
He saved a dangerous Cavani shot with his foot and then turned Christian Maggio's angled effort around the post as the Italians quickly showed their attacking potential with fast, pinpoint passing.
But the visitors went ahead with their first real chance after Napoli captain Paolo Cannavaro sliced Daniel Sturridge's cross and the ball fell at the feet of Mata, who beat Morgan De Sanctis with a first-time shot.
Brazilians David Luiz and Ramires went close for Chelsea as the usually passionate Sao Paolo stadium went eerily quiet. Luiz beat De Sanctis to a corner but his header just cleared the bar while Ramires fired over from the edge of the area.
A last-minute strike by CSKA Moscow newcomer Pontus Wernbloom snatched a 1-1 draw for the Russian side against Real Madrid in their Champions League last 16 first-leg match on Tuesday.
Cristiano Ronaldo had given the visiting Spaniards a deserved 1-0 lead after 28 minutes, taking full advantage of a CSKA defensive mix-up and beating nervous-looking goalkeeper Sergei Chepchugov with a low volley into the far corner.
It was Ronaldo's 17th goal in his 23rd Champions League game for Real and 32nd in total in Europe's premier club competition.
The Portugal striker missed a chance to double the lead shortly after the restart, but this time Chepchugov, making his Champions League debut, averted the danger.
Ronaldo had another opportunity late in the game but fired just wide of the post with a low shot from the edge of the box.
The nine-times European champions dominated for most of the match despite playing in sub-zero temperatures on Luzhniki's unfamiliar artificial pitch but paid dearly for their misses when Sweden midfielder Wernbloom equalised in the last minute of added time following a disputed free kick.
Real coach Jose Mourinho blamed Dutch referee Bjorn Kuipers for the CSKA goal.
"I'm disappointed with the result. We should have scored the second goal, then we would have won for sure," the outspoken Portuguese told Russian television NTV Plus.
But that free kick near the end of the game should have been taken in the opposite direction," he added.
"I must give credit to CSKA as they fought until the end, but the referee had allowed them to play very aggressively and didn't show them any yellow cards."
The home side sorely missed their first-choice keeper Igor Akinfeyev, who is still recovering following knee surgery.
Chepchugov made a fine double save early on, first stopping Gonzalo Higuain, who had just replaced injured Karim Benzema, then denying Sami Khedira from close range seconds later.
The visitors lost France forward Benzema just 15 minutes into the game after he appeared to pull a muscle while taking his first shot on goal.
CSKA's Ivory Coast striker Seydou Doumbia, who has scored five goals in five Champions League games this season, was kept off the ball for most of the match by Real's tight defence.
The Russians struggled to create much of the offence until Wernbloom, who joined CSKA in January, beat Iker Casillas from 10 metres following a goalmouth scramble with virtually the last kick of the game, sending a record 70,000-strong home crowd wild.
"We made a silly mistake in the first half and they punished us. But in the second half we had some extra attackers pushing forward and probably that was the key," said CSKA coach Leonid Slutsky.
"We only had a few chances without playing particularly well but were able to get a goal in the end.
"I think Real are still the favourites but for us anything is possible."