Manchester City’s hopes of qualifying for the knockout stages took a major hit when they lost 2-1 to Napoli at the San Paulo Stadium.
They will now need to beat Bayern Munich in their final game and hope for a favour from Villarreal.
The night was a stark reminder to the Champions League newcomers that this competition represents a major step up for them.
As dominant as City have been in the Premier League this season, they looked rudderless in the final third and created precious few clear cut chances.
City started the match brightly with good build up play allowing both Yaya Toure and Balottelli early chances to get shots on goal.
However despite the Italian side sitting off them for much of the time they were wasteful in the final third, Kolarov in particular guilty of some shocking crosses under no pressure.
Napoli eased there way into the encounter and Ezequiel Lavezzi fired just wide after following a one-two Edison Cavani.
Lavezzi went close again a couple of minutes later with a near post header that Kompany deflected away for a corner.
The duo of Lavezzi and Cavani gave the City defenders problems all night and they combined to give Napoli the lead on 17minutes.
Lavezzi’s corner was flicked on at the near post by Cavani and Joe Hart was unable to keep it out.
Cavani nearly doubled Napoli’s lead just two minutes later with a wicked strike from the edge of the box that hit the side netting.
City were wobbling but some shoddy defending from their generous Italian hosts allowed them a lifeline on 33 minutes.
Salvatore Aronica had ample opportunity to clear the ball but succeeded only in playing the ball into the path of David Silva. The little Spaniard’s shot was saved by De Sanctis but Mario Balotelli was on hand to finish off the rebound.
Napoli emerged for the second half with a renewed purpose and with City uncharacteristically sloppy in possession they were immediately under pressure and fell behind just four minutes after the restart.
It was Cavani once again who did the damage. Such has the Uruguayan been the scourge of Cities defenders that one would half expect to see him dressed in light blue and performing at the Ethiad Stadium come January.
On this occasion he latched onto former Liverpool man Andrea Dossena’s cross and side footed the ball first time past the despairing Hart.
The goal seemed to wake City up and as they had after the first goal they settled into a pattern of keeping possession.
However for the most part they struggled to create chances against a resolute Napoli defence.
Frustration was beginning to get in and Balotelli and Silva were both booked in quick succession for dissent and an off the ball scuffle respectively.
Indeed it was Napoli who looked more threatening on the counter attack. Lavezzi in particular caused defenders all sorts of problems.
Marek Hamsik almost sealed it for the home side with twelve minutes left. The young Slovakian beat Kolarov before firing against the post with Hart well beaten.
Almost immediately City should have been level. Toure’s cross was met by Balotelli who was denied by an unbelievable save from DeSanctis.
The game was really opening up as legs began to tire on both sides. Maggio was played clean through by Lazzari and only a fine save by Hart kept City in the contest.
City needed a spark and Aguero was brought on to replace Dzeko. The Urugyuan’s first major involvement was to win a corner for City. The cross found Ballotelli but his volley was straight at DeSanctis.
That was the last real chance for City. They dominated possession for the remainder of the game but were unable to fashion any quality in the final third.