Paul Robinson conceded for only the second time in qualifying as England lost a crucial encounter against Russia in Moscow.
Robbo earned his 42nd cap as England went down 2-1 after leading through Wayne Rooney's strike.
It means England's destiny is no longer in their hands and if Russia beat Israel away and Andorra at home in their last group fixtures, they will go through to the finals and England will be out.
Dimitar Berbatov scored again for Bulgaria but it was scant consolation as his side could only draw against Albania in Group G. Berba tucked away Martin Petrov's cross three minutes from time but with leaders Romania now out of sight, they have to rely on Holland dropping points against either Luxembourg or Belarus.
Robbie Keane had a couple of efforts at goal on a frustrating night for the Republic of Ireland, who needed Steve Finnan's injury time goal to salvage a 1-1 draw against Cyprus at Croke Park. The Republic's slender chances of qualifying from Group D are now over.
Gareth Bale played another 90 minutes for Wales, who were tested by San Marino in Group D before running out 2-1 winners in Serravalle. Gareth helped set up the second goal, releasing Craig Bellamy who in turn crossed for Joe Ledley to prod home. Wales led 2-0 in the first half, San Marino pegged them back in the second half.
Meanwhile, Teemu Tainio must have been on the edge of his seat all night, even though Finland weren't in action in Group A. Main rivals Portungal were held until the 85th minute before finally breaking down Kazakhstan. Only four points seperate leaders Poland, Portugal, Serbia and Finland with two games left.
Tomas Pekhart made it five goals in four qualifying matches as the Czech Republic Under-21s beat Armenia 3-0 in European U21 Championship qualifying in Kladno. The Czechs scored all three goals in the first half, Tomas grabbing the third.
Didier Zokora played the full 90 minutes as the Ivory Coast lost 3-2 against Euro 2008 co-hosts Austria in Innsbruck. It was an eventful game of three penalties, while Ivory Coast's Steve Gohouri was sent off. Didier Drogba scored twice for Ivory Coast.
It wasn't the best of nights for our players in European Championship qualifying action on Wednesday.