England's hopes of reaching Euro 2008 hang by a thread after Russia came from behind to win in Moscow.
England's Wayne Rooney is dejected at the final whistle
Steve McClaren's side looked on course to qualify courtesy of Wayne Rooney's spectacular 29th-minute volley.
Steven Gerrard missed a glorious chance before Roman Pavluchenko scored from the spot after 69 minutes following Rooney's foul on Konstanin Zurianov.
He struck again from close range four minutes later - now Russia will qualify if they beat Israel and Andorra.
It capped a dramatic turnaround on the Luznikhi Stadium's artificial pitch after England had looked in no trouble until Russia coach Guus Hiddink introduced Pavluchenko in the second half.
Now England's fate is no longer in their own hands, and McClaren will be looking to Israel to get a result against Russia on 17 November to at least keep their hopes alive until the clash with Croatia at Wembley four days later.
England as expected, were without captain John Terry after he suffered a recurrence of his knee injury in training and Sol Campbell came in as replacement.
McClaren will have been perturbed to see the synthetic surface being heavily watered before kick-off, a move clearly designed to make conditions more favourable for Hiddink's side.
Russia had plenty of possession in the early exchanges but England's revamped defence, with Everton's Joleon Lescott in for injured Ashley Cole, protected keeper Paul Robinson.
England suffered an anxious moment after 11 minutes when Aleksandr Kerzhakov tumbled under a challenge from Joe Cole but Spanish referee Luis Medina Cantalejo rightly ignored their penalty claims.
Robinson was called into action when he turned a low drive from Zurianov on to an upright in the 25th minute - and four minutes later England were ahead.
Michael Owen met Micah Richards' punt forward with a prodigious leap, and Rooney was lurking to chest down and lash a brilliant volley high past Russia keeper Vladimir Gabulov.
England survived in comfort until half-time, and should have doubled their advantage four minutes after the interval.
Gareth Barry's free-kick found captain Gerrard totally unmarked at the far post, but he steered a tame finish wide with the goal at his mercy.
And Richards just failed to apply the finishing touch to a Rooney flick as England tried to seal the three points.
Russia took advantage of England's generosity in front of goal to turn the game on its head in the space of four minutes.
Rooney was the villain after 69 minutes, hauling down Zurianov to concede a penalty, even though the initial offence took place outside the area.
Substitute Pavluchenko slammed home the penalty and struck again after 73 minutes, pouncing to score from close range after Robinson parried Alexei Berezutsky's shot.
The dramatic turn in fortunes forced McClaren into a triple substitution, sending on Peter Crouch, Frank Lampard and Stewart Downing for Lescott, Cole and Shaun Wright-Phillips.
But it was Russia who almost added a third when a rebound off Rio Ferdinand bounced inches wide with Robinson beaten.
England threw everything forward in the closing stages, but Russia held out.
Russia: Gabulov, Alexei Berezutsky, Ignashevich, Vasili Berezutsky (Torbinsky 46), Aniukov, Zurianov, Semshov, Bilyaletdinov, Zhirkov, Arshavin (Kolodin 90), Kerzhakov (Pavluchenko 58).
Subs Not Used: Malafeev, Pogrebniak, Shirokov, Sychev.
Booked: Vasili Berezutsky, Pavluchenko.
Goals: Pavluchenko 69 pen, 73.
England: Robinson, Richards, Ferdinand, Campbell, Lescott (Lampard 79), Wright-Phillips (Downing 80), Gerrard, Barry, Cole (Crouch 80), Rooney, Owen.
Subs Not Used: James, Shorey, Luke Young, Neville.
Booked: Ferdinand, Rooney.
Goals: Rooney 29.
Ref: Luis Medina Cantalejo (Spain).