
England, who had a 100 percent qualifying record under Fabio Capello, produced a sub-standard performance and were under constant pressure from the 13th minute when goalkeeper Robert Green was sent off.
Dynamo Kiev striker Andriy Shevchenko missed the resulting spot-kick, but Serhiy Nazarenko ensured Ukraine ran out winners in Dnipropetrovsk when he struck what turned out to be the winner in the 29th minute.
England had already qualified for the World Cup, but their hopes of taking a flawless record to the World Cup looked unlikely after Green was shown a red card for a professional foul on Artem Milevskiy inside the penalty area.
Milevskiy took advantage of a lapse in concentration by Rio Ferdinand and had a clear run on goal before Green brought him down. Referee Skomina did not hesitate to point to the spot before showing Green the red card.
Winger Aaron Lennon made way for goalkeeper David James, whose first task was to face Shevchenko's penalty but the former Chelsea striker could only hit the post and the ball bounced to safety.
Ukraine made amends though as England's defense lost focus for a second time in the match as Ashley Cole conceded possession near the edge of the area and Nazarenko capitalized with a shot which deflected off the Cole's head past a flat-footed James.
Milevskiy struck the woodwork again moments before the half-time interval and Yaroslev Rakytskyy forced James to make a spectacular save after the break as Ukraine continued to dominate.
James saved well again from Andriy Yarmolenko as broke clear before Wayne Rooney missed a late chance to give England an undeserved point.