| Postseason: |
Won World Series (4-2) over Chicago White Sox |

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Transactions listed are from November 1 of previous year to April 1 of the following year.
October 13, 1958
Sent Maury Wills to the Detroit Tigers as part of a conditional deal.
December 4, 1958
Traded Gino Cimoli to the St. Louis Cardinals. Received Wally Moon and Phil Paine.
December 23, 1958
Traded Sparky Anderson to the Philadelphia Phillies. Received Jim Golden, Rip Repulski and Gene Snyder.
December 30, 1958
Released Pee Wee Reese.
1959
Signed Choo Choo Coleman as a free agent.
Signed Bobby Cox as an amateur free agent.
Signed Al Ferrara as an amateur free agent.
Signed Larry Miller as an amateur free agent.
Signed Phil Ortega as an amateur free agent.
Released Elmer Valo.
April 2, 1959 (Standings)
Received Maury Wills from the Detroit Tigers as part of a conditional deal.
May 6, 1959 (Standings)
Traded Dick Hanlon (minors) to the Cincinnati Redlegs. Received Chuck Churn.
May 22, 1959 (Standings)
Traded Jim Baxes to the Cleveland Indians. Received Fred Hatfield and $10,000.
June 5, 1959 (Standings)
Purchased Freddy Rodriguez from the Philadelphia Phillies. (Date given is approximate. Exact date is uncertain.)
June 8, 1959 (Standings)
Sold Solly Drake to the Philadelphia Phillies.
June 9, 1959 (Standings)
Signed Nate Oliver as an amateur free agent.
June 10, 1959 (Standings)
Purchased Cuno Barragan from the Milwaukee Braves. (Date given is approximate. Exact date is uncertain.)
June 15, 1959 (Standings)
Traded Dick Gray to the St. Louis Cardinals. Received Chuck Essegian and Lloyd Merritt.
September 21, 1959 (Standings)
Signed Nick Willhite as an amateur free agent.
October 12, 1959 (Standings)
Cuno Barragan sent to the Milwaukee Braves in an unknown transaction.
October 19, 1959
Traded Jim Gentile to the Baltimore Orioles. Received players to be named later and $50,000. The Baltimore Orioles sent Willy Miranda (March 15, 1960) and Bill Lajoie (minors) (March 15, 1960) to the Los Angeles Dodgers to complete the trade.
November 30, 1959
Steve Bilko drafted by the Detroit Tigers in the 1959 rule 5 draft.
Ray Daviault selected by the San Francisco Giants in the 1959 minor league draft.
Jim Duckworth selected by the Cincinnati Redlegs in the 1959 minor league draft.
1960
Luis Alcaraz received from the Milwaukee Braves in an unknown transaction.
Signed Jim Barbieri as an amateur free agent.
Signed Ken McMullen as an amateur free agent.
Signed Joe Moeller as an amateur free agent.
Signed Thad Tillotson as an amateur free agent.
Signed Hector Valle as an amateur free agent.
Signed Johnny Werhas as an amateur free agent.
April 1, 1960
Traded Clyde Parris (minors) to Toronto (International). Received Joe Altobelli.