In week 4, the Bears played against the Dallas Cowboys on Monday Night Football in Dallas. After a scoreless first quarter and Robbie Gould's field goal, Charles Tillman intercepted Tony Romo, returning the pick for a touchdown. The interception would be the first of Romo's five interceptions. Romo would later hit Miles Austin for a 10-yard touchdown. In the second half, Cutler was able to hit Devin Hester on a 34-yard touchdown pass to extend the Bears lead. Later, Romo's pass was intercepted by Bears linebacker Lance Briggs, who then returned the interception for a touchdown to increase the lead 24-7. The pick-six marked Bears' fourteenth forced turnover, which led the league, and also leads the league in interceptions (11). Cutler would then throw another touchdown pass to Brandon Marshall. Cutler would have his highest performance of the season, completing 18 of 24 passes for 275 yards, along with two touchdowns. His 140.1 passer rating was the third highest of his career. Marshall caught seven passes for 138 yards, a season-best. With 34 seconds left in the game, Romo was replaced by former Bears quarterback Kyle Orton, who threw a 5-yard touchdown pass to Jason Witten, and the Cowboys had a two-point conversion, but the Bears would then win 34-18. With the win, the Bears shared the NFC North lead with the Minnesota Vikings with a 3-1 record.

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