| Postseason: |
Lost World Series (4-1) to Philadelphia Athletics |

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For Bernie. The Rajah. A great Cubs fan and a great dad!
Transactions listed are from November 1 of previous year to April 1 of the following year.
October 3, 1928
Drafted Mike Cvengros from Wichita Falls (Texas) in the 1928 rule 5 draft.
November 7, 1928
Traded Bruce Cunningham, Percy Jones, Lou Legett, Freddie Maguire, Socks Seibold and $200,000 to the Boston Braves. Received Rogers Hornsby.
April 24, 1929 (Standings)
Signed Johnny Schulte as a free agent.
July 6, 1929 (Standings)
Selected Zack Taylor off waivers from the Boston Braves.
October 7, 1929 (Standings)
Drafted Al Shealy from St Paul (American Association) in the 1929 rule 5 draft.
Earl Webb drafted by the Cincinnati Reds in the 1929 rule 5 draft.
October 29, 1929
Selected Les Bell off waivers from the Boston Braves.