Following two consecutive losses to Dallas and San Diego, Philadelphia went to Chicago to take on the Chicago Bears, who were 4-5, on Sunday Night Football. The Eagles dominated the first quarter as Philadelphia took a two score lead on a 25-yard field goal by David Akers and a 13-yard touchdown from Donovan McNabb to Jason Avant on a wide receiver screen pass. Down 10-0 at the start of the second quarter, Chicago drove within one point as Bears kicker Robbie Gould successfully made a 45-yard field goal, as well as a pair of 28-yard field goals, to make the score 10-9 at the half. In the second half, the Bears took the lead as Robbie Gould kicked his fourth field goal, a 49-yarder that put Chicago up 12-10. However, it took only 30 seconds for the Eagles to take the lead as Donovan McNabb passed to DeSean Jackson for a 48-yard touchdown to give the Eagles a 17-12 lead. Ironically, the 48-yard touchdown catch was the shortest touchdown scored by Jackson thus far in the season. Chicago again took the lead in the third quarter as struggling quarterback Jay Cutler, who had already missed several wide open targets in the game, passed to tight end Kellen Davis for a 15-yard score. The Bears converted the 2-point conversion attempt as running back Matt Forte scored on the pass from Cutler to put the Bears back on top 20-17. In the fourth quarter, both defenses fought back and forth but the only points of the final period were scored by Eagles running back LeSean McCoy on a 10-yard, game-winning touchdown run to put the Eagles up 24-20, the game's final score. With the win, the Eagles improved to 6-4. Ironically, the Eagles win came by the same score (24-20) in the same city (Chicago) at the same time and venue (Sunday Night Football on NBC) as when they had lost in week 4 of the 2008 season.

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