Transactions
| Date | Player | Transactions |
| 2/12 | Jason Kipnis, 2B | Signed to a Minor League Contract |
| 2/5 | Ben Taylor, P | Signed to a Minor League Contract |
| 2/2 | Jeremy Jeffress, P | Signed as Free Agent ( 2020)(one-year contract) |
| 1/31 | Corban Joseph, 2B | Signed to a Minor League Contract |
| 1/28 | Steven Souza Jr., RF | Signed as Free Agent ( 2020)(one-year contract) |
| 1/24 | CD Pelham, P | Outrighted to Minors |
| 1/22 | Rex Brothers, P | Signed to a Minor League Contract |
| 1/22 | Danny Hultzen, P | Signed to a Minor League Contract |
| 1/21 | Travis Lakins, P | Traded Boston (for future considerations) |
| 1/17 | Tyler Olson, P | Signed to a Minor League Contract |
| 1/17 | Josh Phegley, C | Signed to a Minor League Contract |
| 1/17 | Casey Sadler, P | Traded Los Angeles (for INF Clayton Daniel) |
| 1/14 | Jason Adam, P | Signed to a Minor League Contract |
| 1/10 | Albert Almora Jr., CF | Signed ( 2020)(avoids arbitration) |
| 1/10 | Javier Báez, SS | Signed ( 2020)(avoids arbitration) |
| 1/10 | Kris Bryant, 3B | Signed ( 2020)(avoids arbitration) |
| 1/10 | Willson Contreras, C | Signed ( 2020)(avoids arbitration) |
| 1/10 | Kyle Ryan, P | Signed ( 2020)(avoids arbitration) |
| 1/10 | Kyle Schwarber, LF | Signed ( 2020)(avoids arbitration) |
| 1/6 | Carlos Asuaje, 2B | Signed to a Minor League Contract |
| 12/20 | Ryan Tepera, P | Signed as Free Agent ( 2020)(one-year contract) |
| 12/18 | Ian Miller, RF | Signed to a Minor League Contract |
| 12/17 | Hernán Pérez, 2B | Signed to a Minor League Contract |
| 12/16 | Noel Cuevas, LF | Signed to a Minor League Contract |
| 12/13 | Brandon Morrow, P | Signed to a Minor League Contract |
| 12/12 | Trevor Megill, P | Drafted Via Rule 5 |
| 12/12 | Brock Stewart, P | Drafted Via Rule 5 (Triple-A phase) |
| 12/6 | Dan Winkler, P | Signed as Free Agent ( 2020)(one-year contract) |
| 12/2 | Jharel Cotton, P | Signed ( 2020)(avoids arbitration) |
| 12/2 | Danny Hultzen, P | Free Agent - No Contract Offer (non-tendered) |
| 12/2 | Addison Russell, SS | Free Agent - No Contract Offer (non-tendered) |
| 11/27 | CD Pelham, P | Acquired Off Waivers Texas |
| 11/23 | Jharel Cotton, P | Traded Oakland (for cash considerations) |
| 11/21 | Dixon Machado, 2B | Signed to Play in Korea (Lotte Giants) |
| 11/20 | Miguel Amaya, C | Purchased From Minors |
| 11/20 | Tyson Miller, P | Purchased From Minors |
| 11/20 | Manuel Rodriguez, P | Purchased From Minors |
| 11/20 | Zack Short, SS | Purchased From Minors |
| 11/4 | David Phelps, P | Declared Free Agency (team option declined) |
| 11/4 | Colin Rea, P | Purchased From Minors |
| 11/4 | Allen Webster, P | Removed From 60-Day IL (Radial nerve inflammation) |
| 11/4 | Allen Webster, P | Outrighted to Minors |
| 11/3 | Tony Barnette, P | Declared Free Agency (team option declined) |
| 11/3 | Kendall Graveman, P | Removed From 60-Day IL (Recovery from right elbow surgery) |
| 11/3 | Kendall Graveman, P | Declared Free Agency (team option declined) |
| 11/3 | Brandon Morrow, P | Removed From 60-Day IL (Recovery from right elbow surgery) |
| 11/3 | Brandon Morrow, P | Declared Free Agency (team option declined) |
| 11/3 | Anthony Rizzo, 1B | Signed ( 2020)(team option exercised) |
| 11/2 | Derek Holland, P | Declared Free Agency (team option declined) |
| 11/2 | José Quintana, P | Signed ( 2020)(team option exercised) |
| 10/31 | Nick Castellanos, 3B | Declared Free Agency |
| 10/31 | Xavier Cedeño, P | Removed From 60-Day IL (Left wrist inflammation) |
| 10/31 | Xavier Cedeño, P | Declared Free Agency |
| 10/31 | Steve Cishek, P | Declared Free Agency |
| 10/31 | Cole Hamels, P | Declared Free Agency |
| 10/31 | Brandon Kintzler, P | Declared Free Agency |
| 10/31 | Jonathan Lucroy, C | Declared Free Agency |
| 10/31 | Pedro Strop, P | Declared Free Agency |
| 10/31 | Ben Zobrist, 2B | Declared Free Agency |
Last updated Feb. 28, 6:00 P.M. ET
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