City are going to need one of their best performances of the season to reach the Europa League quarter-finals after Dynamo Kyiv turned up the heat in a freezing first leg in the Ukrainian capital.
Both of the strikes that inflicted this Round of 16 defeat on Roberto Mancini's side were preventable, but on a night when the Blues looked below par despite a strong line-up on paper, they came as hammer blows.
Only Juventus have prevented City from winning all their Europa League ties at home this season, and next Thursday night now looms as the toughest assignment since the ultimately vain heroics against Hamburg.
If City had expected to be facing a super team following Dynamo's thumping 8-1 aggregate avalanche against the always-handy Turks of Besiktas, they were pleasantly surprised as the game unfolded.
Despite the presence of former powerhouse Andriy Shevchenko, now 34, Kyiv are certainly beatable, and by a three-goal margin, when they arrive for their City of Manchester Stadium test.
Indeed, it might have been the Blues who struck the telling blow early on, when David Silva conjured one of those sublime little passes into the box that sliced the Kyiv defence like a surgeon's fresh scalpel.
Micah Richards had the nous to anticipate that ball and was a split-second from pipping Shovkovskiy to it, but the goalkeeper was brave enough to risk a flying boot and it was the City right-back who came off worst.
That was ten minutes gone. Another ten minutes and Aleks Kolarov, shunted back to left-back by Mancini, found himself on the edge of the area but, having turned and connected well enough, he aimed too close to the keeper.
It was then that Shevchenko showed that old predatory instinct that once marked him out as one of Europe's most effective strikers before the ill-starred move to Chelsea that brought the unhappiest spell of his career
Milevskiy, Dynamo's leading scorer in the Europa League with six goals, turned provider with a 25th-minute cross from the left that landed at the near post for Shevchenko to get ahead of Joe Hart and turn into the City net.
It might have been worse. Milevskiy failed with a blatant attempt to con a penalty out of the German referee, but Shevchenko admirably fought to keep his balance rather than take a tumble under Vincent Kompany's challenge.
And in the second half, it might have been better, particularly if Kolarov's cracking right-foot shot had not been deflected off target for a harmless corner by Khacharedi. Or if Silva had connected with real venom later on.
Unfortunately it was Dynamo who grabbed the all-important goal, undeserved as it was. Gusev had just enough time and space after 77 minutes to chest down and aim true even as Richards launched his attempted block tackle.