| Postseason: |
Lost World Series (4-0) to New York Yankees |

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Transactions listed are from November 1 of previous year to April 1 of the following year.
October 4, 1938
Jimmy Outlaw drafted by the St. Louis Cardinals in the 1938 rule 5 draft.
December 8, 1938
Traded Dusty Cooke to the St. Louis Cardinals. Received Frenchy Bordagaray.
1939
Signed Bobby Adams as an amateur free agent.
Signed Clyde Vollmer as an amateur free agent.
Obtained Mike McCormick from Indianapolis (American Association) as part of a minor league working agreement.
February 14, 1939
Purchased Mel Preibisch from the Pittsburgh Pirates.
February 23, 1939
Sold Al Glossop to the New York Giants.
Returned Woody English to the Brooklyn Dodgers following previous waiver selection.
March 16, 1939
Purchased Billy Werber from the Philadelphia Athletics.
March 17, 1939
Sold Charlie English to the Chicago Cubs for $10,000.
March 20, 1939
Joe Mack assigned from roster onto the St. Louis Cardinals.
May 5, 1939 (Standings)
Gene Schott selected by the Philadelphia Phillies off waivers.
Signed Jimmie Wilson as a free agent.
May 9, 1939 (Standings)
Jim Weaver assigned from roster onto the St. Louis Browns.
June 14, 1939 (Standings)
Traded Earl Cook and cash to the Cleveland Indians. Received Art Jacobs.
July 3, 1939 (Standings)
Traded Charles Glock (minors), Wes Livengood (minors) and Glenn Chapman to the Pittsburgh Pirates. Received Bud Hafey.
August, 1939 (Standings)
Purchased Johnny Niggeling from Indianapolis (American Association).
August 5, 1939 (Standings)
Sold Bud Hafey to the Philadelphia Phillies.
Traded players to be named later and $40,000 to the New York Yankees. Received Vince DiMaggio. The Cincinnati Reds sent Frenchy Bordagaray (January 27, 1940) and Nino Bongiovanni (January 27, 1940) to the New York Yankees to complete the trade.
August 19, 1939 (Standings)
Sold Peaches Davis to the Philadelphia Phillies.
Selected Milt Shoffner off waivers from the Boston Bees.
August 31, 1939 (Standings)
Purchased Al Simmons from the Boston Bees.
October 3, 1939 (Standings)
Paul Gehrman drafted by the Washington Senators in the 1939 rule 5 draft.
October 14, 1939 (Standings)
Drafted Bob Prichard from the Washington Senators in the 1939 minor league draft.
Drafted Hank Sauer from the New York Yankees in the 1939 minor league draft.
October 19, 1939
Released Al Simmons.
December 6, 1939
Traded Les Scarsella and cash to the Boston Bees. Received Jim Turner.
December 7, 1939
Sold Lindsay Brown to Portland (PCL).
1940
Hal Erickson received from Lewiston (Pioneer) in an unknown transaction.
Ed Klieman sent to the Cleveland Indians in an unknown transaction.
Signed Chuck Kress as an amateur free agent.
Signed Johnny Kucab as an amateur free agent.
January 4, 1940
Johnny Niggeling selected by the St. Louis Browns off waivers.
Traded Lee Grissom to the New York Yankees. Received Joe Beggs.
January 29, 1940
Signed Dutch Dietz as a free agent.
February 24, 1940
Le Grant Scott assigned onto roster from the Philadelphia Phillies.