January 03, 2019
Cubs 
sign
Alberto Baldonado
January 10, 2019
February 11, 2019
Cubs
sign
Brad Brach
as a free agent
February 13, 2019
Cubs
place
Kendall Graveman
on the injured list
March 08, 2019
Stephen Ridings
traded from
Cubs
to
Royals
April 10, 2019
Cubs
place
Jon Lester
on the injured list
April 12, 2019
Cubs
place
Victor Caratini
on the injured list
May 08, 2019
Cubs
place
Pedro Strop
on the injured list
June 07, 2019
Cubs
sign
Craig Kimbrel
as a free agent
June 13, 2019
Cubs
place
Carl Edwards
on the injured list
June 15, 2019
Cubs
place
Kyle Hendricks
on the injured list
July 15, 2019
Martin Maldonado
traded from
Royals
to
Cubs
July 16, 2019
Cubs
place
Willson Contreras
on the injured list
July 26, 2019
Derek Holland
traded from
Giants
to
Cubs
July 30, 2019
Cubs
place
Pedro Strop
on the injured list
July 31, 2019
Carl Edwards
traded from
Cubs
to
Padres
Brad Wieck
traded from
Padres
to
Cubs
Nick Castellanos
traded from
Tigers
to
Cubs
Alex Lange
traded from
Cubs
to
Tigers
August 03, 2019
Cubs
designate
Brad Brach
for assignment
August 04, 2019
Cubs
place
Willson Contreras
on the injured list
August 05, 2019
Cubs
place
Craig Kimbrel
on the injured list
Cubs
release
Brad Brach
August 06, 2019
Cubs
place
Brandon Kintzler
on the injured list
August 08, 2019
Cubs
sign
Jonathan Lucroy
as a free agent
August 10, 2019
Cubs
place
Steve Cishek
on the injured list
August 25, 2019
Cubs
place
Derek Holland
on the injured list
September 05, 2019
Cubs
place
Craig Kimbrel
on the injured list
September 07, 2019
Cubs
designate
Taylor Davis
for assignment
October 31, 2019
Steve Cishek
became a free agent
Pedro Strop
became a free agent
Jonathan Lucroy
became a free agent
Brandon Kintzler
became a free agent
Nick Castellanos
became a free agent
November 02, 2019
Derek Holland
became a free agent
November 04, 2019
Kendall Graveman
became a free agent
David Phelps
became a free agent
November 23, 2019
Jharel Cotton
traded from
Athletics
to
Cubs
December 06, 2019
Cubs
sign
Dan Winkler
as a free agent
December 18, 2019
Cubs
sign
Rex Brothers
December 19, 2019
Cubs
sign
Hernan Perez
December 20, 2019
Cubs
sign
Ryan Tepera
as a free agent