Cubs Roster & Staff
Transactions
| Date | Transaction |
| 12/29/20 | Chicago Cubs traded RHP Yu Darvish, C Victor Caratini and cash to San Diego Padres for RHP Zach Davies, SS Reginald Preciado, SS Yeison Santana, OF Ismael Mena and OF Owen Caissie. |
| 12/29/20 | Chicago Cubs traded RHP Yu Darvish, C Victor Caratini and cash to San Diego Padres for RHP Zach Davies, SS Reginald Preciado, SS Yeison Santana, OF Ismael Mena and OF Owen Caissie. |
| 12/29/20 | Chicago Cubs traded RHP Yu Darvish, C Victor Caratini and cash to San Diego Padres for RHP Zach Davies, SS Reginald Preciado, SS Yeison Santana, OF Ismael Mena and OF Owen Caissie. |
| 12/29/20 | Chicago Cubs traded RHP Yu Darvish, C Victor Caratini and cash to San Diego Padres for RHP Zach Davies, SS Reginald Preciado, SS Yeison Santana, OF Ismael Mena and OF Owen Caissie. |
| 12/29/20 | Chicago Cubs traded RHP Yu Darvish, C Victor Caratini and cash to San Diego Padres for RHP Zach Davies, SS Reginald Preciado, SS Yeison Santana, OF Ismael Mena and OF Owen Caissie. |
| 12/29/20 | Chicago Cubs signed free agent LHP Matt Dermody to a minor league contract. |
| 12/29/20 | Chicago Cubs traded RHP Yu Darvish, C Victor Caratini and cash to San Diego Padres for RHP Zach Davies, SS Reginald Preciado, SS Yeison Santana, OF Ismael Mena and OF Owen Caissie. |
| 12/29/20 | Chicago Cubs traded RHP Yu Darvish, C Victor Caratini and cash to San Diego Padres for RHP Zach Davies, SS Reginald Preciado, SS Yeison Santana, OF Ismael Mena and OF Owen Caissie. |
| 12/22/20 | Chicago Cubs claimed RF Phillip Ervin off waivers from . |
| 12/22/20 | Chicago Cubs claimed RF Phillip Ervin off waivers from Seattle Mariners. |
| 12/17/20 | Chicago Cubs signed free agent RHP Jonathan Holder. |
| 12/17/20 | Chicago Cubs signed free agent RHP Jonathan Holder. |
| 12/17/20 | RHP Joe Biagini roster status changed by Chicago Cubs. |
| 12/17/20 | P Joe Biagini roster status changed by Chicago Cubs. |
| 12/16/20 | Chicago Cubs signed free agent 3B Matt Duffy to a minor league contract. |
| 12/16/20 | 3B Matt Duffy roster status changed by Chicago Cubs. |
| 12/14/20 | Chicago Cubs signed free agent RHP Trevor Kelley to a minor league contract. |
| 12/13/20 | Chicago Cubs signed free agent RHP James Bourque to a minor league contract and invited him to spring training. |
| 12/13/20 | Chicago Cubs signed free agent P James Bourque. |
| 12/13/20 | Chicago Cubs signed free agent RHP James Bourque to a minor league contract and invited him to spring training. |
| 12/10/20 | Chicago Cubs claimed RHP Gray Fenter off waivers from . |
| 12/10/20 | Chicago Cubs claimed RHP Gray Fenter off waivers from Norfolk Tides. |
| 12/10/20 | RHP Nicholas Padilla assigned to Chicago Cubs. |
| 12/10/20 | RHP Samuel Reyes assigned to Chicago Cubs. |
| 12/02/20 | Chicago Cubs claimed RHP Robert Stock off waivers from Boston Red Sox. |
| 12/02/20 | CF Albert Almora Jr. elected free agency. |
| 12/02/20 | Chicago Cubs claimed RHP Robert Stock off waivers from . |
| 12/02/20 | LF Kyle Schwarber elected free agency. |
| 12/02/20 | RHP Ryan Tepera elected free agency. |
| 12/02/20 | 1B Jose Martinez elected free agency. |