Andrei Shevchenko and Dynamo Kiev suffered an embarrassing 2-0 defeat at the hands of Moldovan champions FC Sheriff to leave one of the famous names of European football bottom of Europa League Group E.
It was the first time a Moldovan club had triumphed over a Ukrainian side in UEFA competition and Dynamo were undone by first-half goals by Alexander Erokhin and then Brazilian striker Jymmy from the spot as FC Sheriff dominated throughout.
Sheriff went in front in the eighth minute courtesy of Erokhin, their impressive 20-year-old Russian playmaker, who fired in a shot from 25 yards that beat keeper Denys Boyko low to his right.
Dynamo tried to fight back and Oleg Gusev saw his shot blocked by Jose Nadson before Shevchenko's fierce effort from 25 yards was parried by Sheriff keeper Vladislav Stoyanov.
Things went from bad to worse for Dynamo in the 37th minute when Yevhen Khacheridi handballed Milos Adamovic's corner to concede a penalty and found himself booked for good measure.
Jymmy took the spot-kick and made no mistake, placing it low to the right.
Shevchenko's frustration increased and the former Chelsea and AC Milan star was eventually booked for persistent fouling as Dynamo struggled to make any impact in the second half.
Indeed it was Sheriff who came closest to scoring when man-of-the-match Vladimir Brankovic saw his left-footed drive from distance tipped over by Boyko.
With two minutes of normal time remaining Shevchenko had an opportunity to salvage some pride for the Ukrainians after he was fouled by Florent Rouamba 30 yards out.
Shevchenko took the free-kick himself but his effort drifted past the left-hand post without even troubling Vladislav Stoyanov.
That was just about as good as it got for Dynamo and they already look to have a mountain to climb to qualify.