| Postseason: |
Won World Series (4-3) over New York Yankees |

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Transactions listed are from November 1 of previous year to April 1 of the following year.
October 13, 1959
Sold Harry Simpson to the Chicago White Sox.
November 30, 1959
Harry Bright drafted by the Chicago Cubs in the 1959 rule 5 draft.
Drafted Bob Oldis from the New York Yankees in the 1959 rule 5 draft.
Dave Wickersham selected by the Kansas City Athletics in the 1959 minor league draft.
December, 1959
Purchased Pidge Browne from Houston (American Association).
December 9, 1959
Traded a player to be named later, Dick Hall and Ken Hamlin to the Kansas City Athletics. Received Hal Smith. The Pittsburgh Pirates sent Hank Foiles (December 15, 1959) to the Kansas City Athletics to complete the trade.
December 21, 1959
Traded Ron Kline to the St. Louis Cardinals. Received Tom Cheney and Gino Cimoli.
1960
Signed Gene Baker as a free agent.
Signed Steve Blass as an amateur free agent.
Signed Frank Bork as an amateur free agent.
Signed Don Bosch as an amateur free agent.
Bucky Brandon sent to the St. Louis Cardinals in an unknown transaction.
Signed Jose Martinez as an amateur free agent.
Signed Roberto Pena as an amateur free agent.
John Pregenzer sent to the San Francisco Giants in an unknown transaction.
Signed Jim Price as an amateur free agent.
Vic Roznovsky sent to the San Francisco Giants in an unknown transaction.
Signed Tommie Sisk as an amateur free agent.
Signed Gary Waslewski as an amateur free agent.
March, 1960
Received Diomedes Olivo from Poza Rica (Mexican) as part of a conditional deal.
April 7, 1960 (Standings)
The Chicago Cubs returned Harry Bright (earlier draft pick).
May 18, 1960 (Standings)
Sent Jim Campbell to the Chicago White Sox as part of a conditional deal.
May 28, 1960 (Standings)
Traded Ed Bauta and Julian Javier to the St. Louis Cardinals. Received Dick Gray and Vinegar Bend Mizell.
June 1, 1960 (Standings)
Traded Danny Kravitz to the Kansas City Athletics. Received Hank Foiles and cash.
June 2, 1960 (Standings)
Traded Hank Foiles to the Cleveland Indians. Received John Powers.
June 11, 1960 (Standings)
Received Jim Campbell from the Chicago White Sox as part of a conditional deal.
June 24, 1960 (Standings)
Signed Cesar Gutierrez as an amateur free agent.
August 16, 1960 (Standings)
Signed Clem Labine as a free agent.
September 1, 1960 (Standings)
Signed Mickey Vernon as a free agent.
September 3, 1960 (Standings)
Signed Buddy Booker as an amateur free agent.
September 30, 1960 (Standings)
Released Mickey Vernon.
November 28, 1960
Jim Baumer drafted by the Cincinnati Reds in the 1960 rule 5 draft.
Jim Campbell selected by the Milwaukee Braves in the 1960 minor league draft.
Elder White selected by the Chicago Cubs in the 1960 minor league draft.
December 12, 1960
Traded Tom Burgess to Dallas (American Association). Received Don Leppert.
December 16, 1960
Traded Harry Bright, Bennie Daniels and R.C. Stevens to the Washington Senators. Received Bobby Shantz.
1961
Signed Bob Bailey as an amateur free agent.
Signed Jerry May as an amateur free agent.
Signed Dave Wissman as an amateur free agent.
February, 1961
Sold Paul Giel to the Minnesota Twins.
April, 1961
Released Pidge Browne. (Date given is approximate. Exact date is uncertain.)