Transactions
| Date | Player | Transactions |
| 2/20 | Sergio Alcántara, SS | Outrighted to Minors |
| 2/20 | Phillip Ervin, LF | Designated for Assignment |
| 2/20 | Jake Marisnick, CF | Signed as Free Agent ( 2021; Opt 2022)(one-year contract) |
| 2/20 | Cameron Maybin, CF | Signed to a Minor League Contract |
| 2/19 | Ian Happ, CF | Signed ( 2021)(wins arbitration) |
| 2/17 | Sergio Alcántara, SS | Designated for Assignment |
| 2/17 | Cody Allen, P | Retired |
| 2/17 | Jake Arrieta, P | Signed as Free Agent ( 2021; Opt 2022)(one-year contract) |
| 2/17 | Kyle Ryan, P | Placed on 10-Day IL (COVID-19 injured list (positive test)) |
| 2/17 | Pedro Strop, P | Signed to a Minor League Contract |
| 2/17 | Brandon Workman, P | Signed as Free Agent ( 2021)(one-year contract) |
| 2/12 | José Lobatón, C | Signed to a Minor League Contract |
| 2/5 | Sergio Alcántara, SS | Acquired Off Waivers Detroit |
| 2/5 | Andrew Chafin, P | Signed as Free Agent ( 2021; Opt 2022)(one-year contract) |
| 2/5 | Joc Pederson, CF | Signed as Free Agent ( 2021; Opt 2022)(one-year contract) |
| 2/5 | Max Schrock, 2B | Designated for Assignment |
| 2/5 | Trevor Williams, P | Signed as Free Agent ( 2021)(one-year contract) |
| 2/4 | Joe Biagini, P | Signed to a Minor League Contract |
| 2/4 | Rex Brothers, P | Signed to a Minor League Contract |
| 1/28 | Kohl Stewart, P | Signed as Free Agent ( 2021)(one-year contract) |
| 1/22 | Austin Romine, C | Signed as Free Agent ( 2021)(one-year contract) |
| 1/20 | Matt Dermody, P | Released |
| 1/20 | Matt Dermody, P | Signed to Play in Japan (Seibu Lions) |
| 1/17 | Shelby Miller, P | Signed to a Minor League Contract |
| 1/15 | Javier Báez, SS | Signed ( 2021)(avoids arbitration) |
| 1/15 | Kris Bryant, 3B | Signed ( 2021)(avoids arbitration) |
| 1/15 | Willson Contreras, C | Signed ( 2021)(avoids arbitration) |
| 1/15 | Zach Davies, P | Signed ( 2021)(avoids arbitration) |
| 1/8 | Nick Martini, LF | Signed to a Minor League Contract |
| 1/8 | Patrick Wisdom, 3B | Signed to a Minor League Contract |
| 1/6 | Colin Rea, P | Cleared Waivers and Became a Free Agent |
| 1/4 | Adam Morgan, P | Signed to a Minor League Contract |
| 1/4 | Colin Rea, P | Released |
| 12/29 | Owen Caissie, RF | Traded San Diego (for RHP Yu Darvish, seven-player deal) |
| 12/29 | Zach Davies, P | Traded San Diego (for RHP Yu Darvish, seven-player deal) |
| 12/29 | Reginald Preciado, SS | Traded San Diego (for RHP Yu Darvish, seven-player deal) |
| 12/23 | Matt Dermody, P | Signed to a Minor League Contract |
| 12/22 | Phillip Ervin, LF | Acquired Off Waivers Seattle |
| 12/21 | Matt Duffy, 3B | Signed to a Minor League Contract |
| 12/19 | D.J. Snelten, P | Signed to a Minor League Contract |
| 12/18 | James Bourque, P | Signed to a Minor League Contract |
| 12/17 | Jonathan Holder, P | Signed as Free Agent ( 2021)(one-year contract) |
| 12/10 | Gray Fenter, P | Drafted Via Rule 5 |
| 12/2 | Albert Almora Jr., CF | Free Agent - No Contract Offer (non-tendered) |
| 12/2 | Michael Hermosillo, RF | Signed to a Minor League Contract |
| 12/2 | José Martínez, LF | Free Agent - No Contract Offer (non-tendered) |
| 12/2 | Colin Rea, P | Signed ( 2021)(avoids arbitration) |
| 12/2 | Kyle Ryan, P | Signed ( 2021)(avoids arbitration) |
| 12/2 | Kyle Ryan, P | Free Agent - No Contract Offer (non-tendered) |
| 12/2 | Kyle Ryan, P | Signed as Free Agent ( 2021)(one-year contract) |
| 12/2 | Kyle Schwarber, LF | Free Agent - No Contract Offer (non-tendered) |
| 12/2 | Robert Stock, P | Acquired Off Waivers Boston |
| 12/2 | Ryan Tepera, P | Free Agent - No Contract Offer (non-tendered) |
| 12/2 | Dan Winkler, P | Signed ( 2021)(avoids arbitration) |
| 12/2 | Dan Winkler, P | Free Agent - No Contract Offer |
| 12/2 | Dan Winkler, P | Signed as Free Agent ( 2021)(one-year contract) |
| 11/20 | Cory Abbott, P | Purchased From Minors |
| 11/20 | Christopher Morel, 3B | Purchased From Minors |
| 11/20 | Keegan Thompson, P | Purchased From Minors |
| 11/19 | Ian Miller, RF | Signed to a Minor League Contract |
| 11/16 | Jake Jewell, P | Signed to a Minor League Contract |
| 11/16 | Jerry Vasto, P | Signed to a Minor League Contract |
| 11/15 | Rafael Ortega, LF | Signed to a Minor League Contract |
| 11/5 | Abiatal Avelino, SS | Signed to a Minor League Contract |
| 11/2 | Danny Hultzen, P | Declared Free Agency |
| 11/2 | Tyler Olson, P | Declared Free Agency |
| 11/2 | Pedro Strop, P | Declared Free Agency |
| 11/2 | Jerry Vasto, P | Declared Free Agency |
| 11/2 | Mark Zagunis, RF | Declared Free Agency |
| 11/1 | James Norwood, P | Removed From 60-Day IL (Right shoulder inflammation) |
| 11/1 | Brad Wieck, P | Removed From 60-Day IL (Strained right hamstring) |
| 10/31 | Rex Brothers, P | Refused Minor League Assignment - Free Agent |
| 10/31 | Daniel Descalso, 2B | Removed From 60-Day IL (Sprained left ankle) |
| 10/31 | Daniel Descalso, 2B | Declared Free Agency (team option declined) |
| 10/31 | Anthony Rizzo, 1B | Signed ( 2021)(team option exercised) |
| 10/31 | Manuel Rodríguez, P | Removed From 60-Day IL (Strained right biceps) |
| 10/30 | Rex Brothers, P | Outrighted to Minors |
| 10/30 | Jon Lester, P | Declared Free Agency (mutual option declined) |
| 10/30 | Max Schrock, 2B | Acquired Off Waivers St. Louis |
| 10/28 | Andrew Chafin, P | Declared Free Agency |
| 10/28 | Tyler Chatwood, P | Declared Free Agency |
| 10/28 | Billy Hamilton, CF | Declared Free Agency |
| 10/28 | Jeremy Jeffress, P | Declared Free Agency |
| 10/28 | Jason Kipnis, 2B | Declared Free Agency |
| 10/28 | Cameron Maybin, CF | Declared Free Agency |
| 10/28 | Josh Phegley, C | Declared Free Agency |
| 10/28 | José Quintana, P | Declared Free Agency |
| 10/28 | Mark Zagunis, RF | Reinstated From Restricted List |
| 10/14 | Ian Miller, RF | Refused Minor League Assignment - Free Agent |
| 10/7 | Patrick Wisdom, 3B | Refused Minor League Assignment - Free Agent |
| 10/2 | Josh Osich, P | Outrighted to Minors |
| 10/2 | Josh Osich, P | Refused Minor League Assignment - Free Agent |
Last updated Feb. 25, 4:39 P.M. ET
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