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Friday, September 15, 1939 - 8:30PM
Cleveland Rams  21  vs
at Soldier Field, Chicago, IL
Due to temperatures exceeding 90 degrees for a night game, the Bears wore orange jerseys during the 1st Half and switched to plain white jerseys for the 2nd Half.
Sunday, September 24, 1939 - 3:00PM
Chicago Bears  16  vs
at City Stadium, Green Bay, WI
Monday, October 2, 1939 - 9:00PM
Chicago Bears  32  vs
at Forbes Field, Pittsburgh, PA

Sunday, October 8, 1939 - 2:15PM
Chicago Bears  35  vs
at Cleveland Municipal Stadium, Cleveland, OH
Bears wore orange jerseys during the 1st Half and changed to plain white jerseys for the 2nd Half.
Sunday, October 15, 1939 - 2:15PM
at Wrigley Field, Chicago, IL
Sunday, October 22, 1939 - 2:30PM
Chicago Bears  13  vs
at Polo Grounds, New York, NY

Sunday, October 29, 1939 - 3:15PM
Detroit Lions  10  vs
at Wrigley Field, Chicago, IL
Sunday, November 5, 1939 - 3:00PM
at Wrigley Field, Chicago, IL
Sunday, November 12, 1939 - 2:00PM
Chicago Bears  23  vs
at Briggs Stadium, Detroit, MI

Sunday, November 19, 1939 - 3:00PM
at Wrigley Field, Chicago, IL
Sunday, November 26, 1939 - 3:00PM
Chicago Bears  48  vs
at Wrigley Field, Chicago, IL