Russia fought back from one goal down to leave England's hopes of qualifying for Euro 2008 hanging by the narrowest of threads following a 2-1 defeat in Moscow.
Substitute Roman Pavluychenko stepped off the bench to score twice and leave Steve McClaren's side hoping for a minor miracle in order to reach next summer's final in Austria and Switzerland.
England remain second behind Group E leaders Croatia, but should Russia win their game in hand against Israel and then defeat Andorra in their final qualifying match, then they will progress to the finals at the expense of McClaren's side.
It had all started so positively on the controversial synthetic pitch inside Moscow's Luzhniki Stadium as Wayne Rooney fired the visitors into a first-half lead with a thunderbolt of a 29th-minute volley.
Russia had started at a high tempo and Konstantin Zyrianov had gone close with a low drive which Paul Robinson pushed on to the post before Rooney broke the deadlock in sensational style.
The Manchester United striker controlled a flick from Michael Owen on his chest before rifling an unstoppable volley beyond the static Vladimir Gabulov from just inside the penalty area.
England should have doubled their lead and perhaps killed off Russian hopes with two clear-cut chances just after half-time.
Firstly, Steven Gerrard scuffed a close-range volley wide of the back post when ghosting in unmarked onto a Gareth Barry free-kick.
Then Micah Richards was inches away from stabbing Rooney's flick from a wicked Gerrard free-kick beyond the keeper from the edge of the six-yard box.
England were to pay for their profligacy as Russia were awarded a controversial 68th minute penalty when Rooney was adjudged to have brought down Konstantin Zyrianov.
Rooney clipped the midfielder's heels but the contact appeared to have taken place outside the area.
However, Pavluychenko, who had only been on the pitch for ten minutes, kept his nerve to drill the spot-kick low and to Robinson's right to draw the scores level.
Then, with England rocking, Pavluychenko did it again as he reacted quicker than Joleon Lescott and Sol Campbell to force the loose ball home after Robinson had palmed away Alexey Berezutsky's angled shot.
England made a desperate triple change by sending on Frank Lampard, Stewart Downing and Peter Crouch for the final ten minutes, but they were unable to break down the red wall that had been erected in front of Gabulov's goal.
Three minutes of stoppage time were added but McClaren's side were continually repelled and now seem certain to be spending next summer on extended holidays rather than playing in the European Championship after a cruel twist of fate.