Middlesbrough inflicted Arsenal's first Premier League defeat of the season with a 2-1 win on Sunday to cut the Gunners' lead over Manchester United at the top of the table to just one point.
In the day's other matches, Bolton heaped more misery on second-bottom Wigan with a 3-1 win, while Tottenham secured only their third league win of the season with a 2-1 success against a Manchester City side that finished the game with 10 men after Stephen Ireland was sent off.
Defeat meant Sven-Goran Eriksson's City missed out on the chance to go above Liverpool and into fourth place in the table, while Spurs are now two points clear of the bottom three.
West Ham continued their fine recent form with a 1-0 win away to Blackburn Rovers, which left the Londoners 10th as Alan Curbishley celebrated a year in charge with a victory.
Stewart Downing, with a fourth-minute penalty, and Tuncay Sanli, with a close-range strike 16 minutes from time, scored for Middlesbrough at the Riverside.
Tomas Rosicky pulled a goal back in the fifth minute of stoppage time, but it was too late for Arsenal.
The result gave Middlesbrough, who started Sunday in the relegation zone, only their third win in the Premiership this season.
Just as in Wednesday's 1-1 draw against Newcastle, Arsenal were without key midfielders Cesc Fabregas, Mathieu Flamini and Alexander Hleb and the result revived concerns over whether they have a strong-enough squad to sustain a title challenge.
But Arsenal manager Arsene Wenger had no complaints about the result.
"We lost the game because we deserved to lose it," he said. "It's that simple. Middlesbrough were sharper in the fight. We missed the start of the game by giving them too much room and it cost a penalty."
Middlesbrough manager Gareth Southgate, whose side ended a run of 11 games without a win and climbed out of the bottom three, said he felt the fixture schedule would work against Arsenal.
"I felt Arsenal having three games in a week was a tall order for them and thought it might be a good day to get them," former England defender Southgate said.
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