Fenerbahce 2 Chelsea 1: Former Sheffield United forward Colin Kazim-Richards led the fightback for Fenerbahce at a hostile Sukru Saracoglu Stadium to leave Chelsea's Champions League hopes in the balance.
Avram Grant's men were leading through an own goal by Deivid in the first half and could have extended their lead before Kazim-Richards came on in the 54th minute.
His goal came 10 minutes later and Deivid added a spectacular second, leaving Chelsea needing to win at Stamford Bridge next week to reach their fourth semi-final in five years.
The visitors had not conceded a goal in their previous six Champions League games and the Turks initially looked like they would not trouble them either. Fenerbahce attacked as they promised but Mateja Kezman had the type of frustrating evening he often endured during his brief spell at Stamford Bridge.
Hostility erupted every time Chelsea enjoyed possession, then home fans urged Fenerbahce forward when they had the ball. It could hardly be said that Chelsea silenced the home fans as they were as noisy after the opener as they were at kick-off.
How the visitors threw it away will frustrate Grant as it was a first-half masterclass from Chelsea in playing away from home in Europe.
Their opener, however, came from a huge slice of luck. Ballack dummied the ball for Florent Malouda to chase down the left flank, his cross was powerful and low but not heading towards a team-mate — and Deivid shanked the ball past goalkeeper Volkan Demirel and into the near post.
Michael Essien could have doubled the lead five minutes later but his 30-yard drive, swerving away from Demirel, hit the crossbar. Essien then crossed for Drogba to leap over Onder Turaci but head just wide.
Desperate for a goal, Drogba had options the next time he went through but shot disappointingly wide.
Alex glanced a header just wide after the break, and the Brazilian kicked the post in frustration at spurning the hosts' best chance of the match.
Kezman also tried his luck with a scissor-kick that Cudicini saved at the near post.
Drogba threatened with a couple of long-range efforts, and Ballack forced a save from Demirel with a powerful drive, with the rebound just eluding Malouda.
But for all of Chelsea's pressure, Kazim-Richards was brought on and grabbed the equaliser in the 65th minute, latching onto Aurelio's through-ball and smashing past Cudicini.
Ballack could have restored the lead in the next move when he raced through — but Demirel saved. Deivid's goal came nine minutes from the final whistle. He picked the ball up 35 yards out and sent it whistling into Cudicini's top corner.
Nicolas Anelka was brought on for Chelsea but the jeers, and the defeat, made it a forgettable return to his former club.