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Friday, September 15, 1939 - 8:30PM
Cleveland Rams  21  vs
at Wrigley 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
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