Dallas Cowboys lead series 15-12-0 The following is a list of all regular season and postseason games played between the Chicago Bears and Dallas Cowboys. The two teams have met each other 27 times (including 2 postseason games), with the Chicago Bears winning 12 games and the Dallas Cowboys winning 15 games. Dallas Cowboys lead series 15-12-0 The two teams have met each other 27 times (including 2 postseason games), with the Dallas Cowboys winning 15 games and the Chicago Bears winning 12 games. The following is a list of all regular season and postseason games played between the Dallas Cowboys and Chicago Bears. Bears vs. Cowboys Recent History – First Meeting Since 2016 Dallas is riding a two-game winning streak versus Chicago.