Cubs Roster & Staff
Transactions
| Date | Transaction |
| 10/31/20 | 2B Daniel Descalso elected free agency. |
| 10/30/20 | Chicago Cubs claimed 2B Max Schrock off waivers from St. Louis Cardinals. |
| 10/30/20 | Chicago Cubs sent LHP Rex Brothers outright to Iowa Cubs. |
| 10/28/20 | 2B Jason Kipnis elected free agency. |
| 10/28/20 | LHP Andrew Chafin elected free agency. |
| 10/28/20 | LHP Jose Quintana elected free agency. |
| 10/28/20 | LF Cameron Maybin elected free agency. |
| 10/28/20 | RHP Jeremy Jeffress elected free agency. |
| 10/28/20 | CF Billy Hamilton elected free agency. |
| 10/28/20 | RHP Tyler Chatwood elected free agency. |
| 10/28/20 | C Josh Phegley elected free agency. |
| 10/22/20 | Chicago Cubs sent RF Mark Zagunis outright to Iowa Cubs. |
| 10/21/20 | Chicago Cubs activated RF Mark Zagunis from the restricted list. |
| 10/15/20 | Chicago Cubs signed free agent RHP Joandy Duran to a minor league contract. |
| 10/15/20 | Chicago Cubs signed free agent IF Andrws Cruz to a minor league contract. |
| 10/15/20 | Chicago Cubs signed free agent SS Leonel Espinoza to a minor league contract. |
| 10/15/20 | Chicago Cubs signed free agent RHP Yohan Crispin to a minor league contract. |
| 10/15/20 | Chicago Cubs signed free agent RHP Jose Lopez to a minor league contract. |
| 10/15/20 | Chicago Cubs signed free agent LHP Angel Hernandez to a minor league contract. |
| 10/15/20 | Chicago Cubs signed free agent OF Jerry Torres to a minor league contract. |
| 10/15/20 | Chicago Cubs signed free agent C Jose Herrera to a minor league contract. |
| 10/15/20 | Chicago Cubs signed free agent RHP Jose Romero to a minor league contract. |
| 10/15/20 | Chicago Cubs signed free agent RHP Waimer Fabian to a minor league contract. |
| 10/15/20 | Chicago Cubs signed free agent LHP Marino Santy to a minor league contract. |
| 10/04/20 | Chicago Cubs signed free agent RHP Juan Gamez to a minor league contract and invited him to spring training. |
| 10/04/20 | Chicago Cubs signed free agent P Juan Gamez. |
| 10/04/20 | Chicago Cubs signed free agent RHP Juan Gamez to a minor league contract and invited him to spring training. |
| 10/03/20 | Chicago Cubs activated P Dillon Maples. |
| 10/03/20 | Chicago Cubs activated RHP Dillon Maples. |
| 10/03/20 | Chicago Cubs activated RHP Duane Underwood Jr.. |
| 10/03/20 | Chicago Cubs activated RHP Tyson Miller. |
| 10/03/20 | Chicago Cubs activated LHP Brailyn Marquez. |
| 10/03/20 | Chicago Cubs activated RHP Rowan Wick. |
| 10/03/20 | Chicago Cubs activated RHP Colin Rea. |
| 10/03/20 | Rex Brothers roster status changed by Chicago Cubs. |
| 10/03/20 | Chicago Cubs activated C Miguel Amaya. |
| 10/03/20 | Chicago Cubs activated 1B Jose Martinez. |
| 10/03/20 | Chicago Cubs activated LHP Justin Steele. |
| 10/03/20 | Chicago Cubs activated RHP Dillon Maples. |
| 10/03/20 | Chicago Cubs activated CF Albert Almora Jr.. |
| 10/03/20 | Chicago Cubs activated RHP Tyler Chatwood. |
| 10/02/20 | Chicago Cubs sent LHP Josh Osich outright to Cubs Alternate Training Site. |