Robert Green became the first England goalkeeper to be sent off as Fabio Capello saw his 100% World Cup record smashed to pieces by the Ukraine.
Green was dismissed for a professional foul just 15 minutes into what turned out to be one of the worst defensive performances in Capello's time in charge.
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.
Ashley Cole's attempt to atone for an equally crass mistake resulted in him turning Serhiy Nazarenko's shot past David James.
And neither Glen Johnson, nor normally rock-solid skipper John Terry were much better as Capello experienced defeat in a competitive game for the first time.
Along with a few others, it really was not Green's night.
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.
Prior to only his second competitive start in 12 months, Ferdinand spoke of the unspoken knowledge that no-one in Capello's squad can feel sure of their place in South Africa.
In truth, it would be a startling development if the defender did not go.
Yet fitness concerns remain, despite his claim that he is now fully fit.
But neither injury, nor rustiness could be used as an excuse for the rank bad defending that let Artem Milevskiy charge straight through the heart of England's rearguard.
Green came out to confront the striker but only succeeded in sending him sprawling.
In the confusion that followed referee Damir Skomina initially showed Ferdinand a red card before finally sending Green on his way.
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 Andriy 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 to allow England to continue their dream of completing a perfect qualifying campaign.
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 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.
Cue more flares - and a threat to stop the game, which would actually have been no bad thing as errors continued to undermine England's hopes of pulling level.
Another Ferdinand blunder almost proved costly when the defender's loose header fell to the impressive Milevskiy, whose thunderous shot cannoned back off a post with James hopelessly beaten.
So, while Frank Lampard almost profited from Rooney's astute pass, Capello's half-time demand was for clearer focus, although the loss of Steven Gerrard at half-time shut off one obvious avenue of redemption.
Lampard drove a free-kick into the wall when set to do much better and Rooney's industry almost brought England level near the end in a late surge as Ukraine sweated.
But an equaliser would have been unjust given the sheer volume of basic defensive mistakes, which must have left Capello shell-shocked.
James Milner conceded a corner at the end of a catalogue of clangers, then James needed to make a feet-first save to deny Andriy Yarmolenko, who had been put clean through by Yaroslav Rakitskiy.
It was almost too bad to be true.
Conspiracy theorists wondered whether England might be secretly happy to lose, just to ensure Croatia are knocked out, which will be the case if Ukraine complete the relatively straightforward task of beating Andorra on Wednesday.
If that was supposed to be a consolation, it was totally lost on Capello, who can only hope his players have had all their bad luck and endured all their calamities on one night.
For if they repeat this showing, with 10 men or 11 in South Africa next year, they won't be away from home very long.