January 13, 2020

January 17, 2020

Casey Sadler traded from Dodgers  to Cubs 

January 21, 2020

Travis Lakins traded from Red Sox  to Cubs 

January 28, 2020

Cubs  sign Steven Souza as a free agent

January 30, 2020

Cubs  sign Jason Adam

July 14, 2020

Cubs  sign Jose Lobaton

July 23, 2020

Cubs  place Jose Quintana on the injured list

Cubs  designate Robel Garcia for assignment

Cubs  sign Ryan LaMarre

July 26, 2020

Cubs  place Brad Wieck on the injured list

August 02, 2020

Cubs  place James Norwood on the injured list

August 16, 2020

Cubs  place Tyler Chatwood on the injured list

Cubs  designate Jharel Cotton for assignment

August 18, 2020

Cubs  place Steven Souza on the injured list

August 22, 2020

Cubs  place Kris Bryant on the injured list

August 23, 2020

Cubs  sign Patrick Wisdom

August 31, 2020

Cubs  designate Hernan Perez for assignment

Andrew Chafin traded from Diamondbacks  to Cubs 

Josh Osich traded from Red Sox  to Cubs 

September 01, 2020

Cubs  place Tyler Chatwood on the injured list

Cubs  designate Casey Sadler for assignment

September 02, 2020

Cubs  place Jose Quintana on the injured list

September 03, 2020

Cubs  release AJ Ramos

September 05, 2020

Cubs  release Jharel Cotton

Cubs  sign Pedro Strop

September 06, 2020

Cubs  designate Steven Souza for assignment

September 07, 2020

Cubs  designate Matt Dermody for assignment

Cubs  release Jose Lobaton

September 08, 2020

Cubs  release Steven Souza

September 10, 2020

Cubs  release Ryan LaMarre

September 19, 2020

Cubs  place Rowan Wick on the injured list

September 21, 2020

Cubs  place Ildemaro Vargas on the injured list

September 25, 2020

Cubs  place Manuel Rodriguez on the injured list

September 27, 2020

Cubs  designate Patrick Wisdom for assignment

September 28, 2020

Matt Dermody became a free agent

September 30, 2020

Cubs  designate Josh Osich for assignment

October 28, 2020

Cameron Maybin became a free agent

Andrew Chafin became a free agent

Tyler Chatwood became a free agent

Jose Quintana became a free agent

Billy Hamilton became a free agent

October 30, 2020

Jon Lester became a free agent

November 12, 2020

Cubs  sign Michael Hermosillo

November 16, 2020

Cubs  sign Jake Jewell

Cubs  sign Rafael Ortega

Cubs  sign Taylor Gushue

December 02, 2020

Ryan Tepera became a free agent

Albert Almora became a free agent

Kyle Schwarber became a free agent

December 14, 2020

Cubs  sign Trevor Kelley

December 16, 2020

Cubs  sign Matt Duffy

December 29, 2020

Cubs  sign Matt Dermody