Serhiy Nazarenko scored the only goal as Ukraine beat Group 6 winner England 1-0 in World Cup qualifying on Saturday to strengthen its chances of reaching the finals.
Nazarenko scored in the 29th minute to end England’s winning run of eight qualifiers after Andriy Shevchenko had missed a penalty and England had goalkeeper Robert Green sent off in the 13th minute for taking down Artem Milevskiy inside the area.
The result leaves England with 24 points from nine games and Ukraine has overtaken Croatia in second place with 18 points. A win over Andorra on Wednesday would secure Ukraine the runners-up slot ahead of Croatia, which is now one point behind.
The eight best runners up in the nine groups qualify for the playoffs in November.
England coach Fabio Capello remonstrated with the referee after the game, but his side produced little of the form shown in its previous qualifiers.
The match had to be stopped after just one minute after dozens of flares were thrown into England’s penalty area. After a short break while the flares were cleared away, the first chance fell to England, with Emile Heskey heading over after Aaron Lennon drove into the area from the right.
The match then sparked into life when Milevskiy beat the England defence to a long ball, only to be brought down by Green after slipping the ball past him. The referee promptly showed the goalkeeper a red card and veteran David James came on to face the penalty in place of Lennon.
Ukraine captain Andriy Shevchenko stepped up to take it, but put his attempt wide off the bottom of the post with James.
The home crowd reacted by bombarding James’ penalty area with more flares.
Ukraine was now on the front foot, however, and the pressure told in the 29th minute when Nazarenko, playing on his home ground, lashed a shot from the edge of the area off Ashley Cole and past the diving James.
England could have been back on level terms immediately, but Frank Lampard stroked his shot across the goal and just wide after being played in by Wayne Rooney from the right.
Ukraine could have doubled its lead on 32 minutes when Milevskiy hit the bar with a crashing drive from 25 meters after good work in the air by Ruslan Rotan.
With Heskey now playing alone up front, England’s most promising attacks came down the right, with Glen Johnson looking threatening. He did well to get to the byline in the 40th minute, but the goalkeeper easily dealt with the cross.
England came out in the second half looking to put pressure on Ukraine’s defence, which looked solid despite a number of changes enforced by injury and suspension. In fact, Ukraine looked more likely to extend its lead and a diving James had to push a stinging drive from 30 meters by Yaroslav Rakytskiy past his right-hand post on 54 minutes.
England’s best chance fell to Lampard, who was played through by Rooney in the 60th minute, but his first touch was too strong. Lampard had another opportunity on 68 minutes after being brought down right on the edge of the box, but he drove his free kick straight into the wall.
England rarely threatened and Ukraine almost made certain of victory in the 80th minute when substitute Andriy Yarmolenko was put through on goal, but James blocked his shot.
Rooney could have levelled on the stroke of full time, but pulled his shot from the edge of the box just wide of the post. After three tense minutes of injury time, the final whistle went to send Ukraine to Andorra with every chance of making the playoffs.