Dynamo Kiev 2 Manchester City 0: Manchester City will need to display all their attacking strength next week if they are to remain in the Europa League.
They are chasing a two-goal deficit after former Chelsea striker Andriy Shevchenko and Oleh Gusev handed Dynamo Kiev a useful advantage in this last-16 first leg match.
To complete a frustrating night for manager Roberto Mancini, Mario Balotelli came off in the second half with the Italian striker claiming to be unwell.
After a bright start City showed nothing like the kind of form that marked them down as tournament favourites.
They knew it would be a tough test in freezing conditions as Dynamo went into the match having lost only one of their past 16 games.
With Carlos Tevez on the bench Gareth Barry was handed the captain's armband.
David Silva threaded the ball through to Micah Richards in the 11th minute only for goalkeeper Olexandr Shovkovskly to block his path.
Balotelli then tried to release Edin Dzeko in the 18th minute only to put too much weight on the pass and the ball drifted out of play.
City kept up the momentum and won a free-kick 25 yards out but Aleksandar Kolarov sent his effort into the goalkeeper's body.
Dynamo took the lead with their first attempt in the 24th minute when Shevchenko poked home a cross from Andriy Yarmolenko.
Balotelli was late arriving for the start of the second half and appeared to be in some distress.
Mancini, however, was in no hurry to take him off and Balotelli suffered further misery in the 54th minute when he was booked for a challenge on Ayila Yussuf.
Three minutes later Balotelli headed for the dressing room and was replaced by Tevez.
City almost drew level in the 59th minute when Barry laid the ball back to Yaya Toure on the edge of the area. He struck his shot sweet and true only for the goalkeeper to turn it around the post.
City's troubles increased in the 77th minute when Dynamo forged 2-0 ahead after poor defending.
Richards failed to deal with a flick on from Milevskiy and Gusev smashed a volley home from eight yards.