Robert Green became the first England goalkeeper to be sent off as Fabio Capello's 100% World Cup record was smashed to pieces after Serhiy Nazarenko's deflected goal earned Ukraine a 1-0 victory.
Nazarenko's shot struck Ashley Cole and flew past substitute goalkeeper David James for the 30th minute decider to halt already-qualified England's run of eight successive wins.
James came on for Green, who was sent off for bringing down Artem Milevskiy in the 13th minute but Andriy Shevchenko's spot-kick hit the post.
Wayne Rooney is exempt from criticism after a towering display which he nearly capped with a last-minute equaliser. But at the back, it was a collective nightmare.
Rio Ferdinand's return to competitive action turned out to be pretty disastrous, making the error that eventually resulted in Green's departure and Ashley Cole's attempt to atone for an equally crass mistake resulted in him turning Nazarenko's shot past David James.
Pelted with flares seconds into the game that resulted in a two-minute hold-up, Green had barely had a touch when Ferdinand made his aberration. Green came out to confront Milevskiy but only succeeded in sending him sprawling.
David James was his replacement, Aaron Lennon the unlucky man replaced. After just 15 minutes, it was a major disruption Capello could have done without and the Italian must have had a sense of foreboding as Shevchenko strode up to take the spot-kick given the number of times the Ukrainian hero has scored against him in the past. Not this time though. This time he smacked the outside of a post.
For a while, the Three Lions were quite comfortable. They even managed to get forward on a couple of occasions, Rooney predictably getting through the work of two men to make up the numbers.
But when Cole also made a needless error close to his own penalty area there was no reprieve as Milevskiy drove forward before the ball eventually broke to Nazarenko after Glen Johnson had made a tackle.
On the ground where he plays his club football, Nazarenko let fly with relish. Cole flung himself at the ball in a bid to make amends. But he could only divert it into the corner, ending any hope James had of keeping it out.
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