| Week | Add | Drop |
| Week 1 |
Round 1: SS Oswaldo Cabrera - NYA | |
| Week 2 |
Round 1: SP Cody Bradford - Tex |
Round 1: SP Kyle Hendricks - ChN |
| Week 3 |
Round 1: SP Dane Dunning - Tex Round 2: 3B Anthony Rendon - LAA | |
| Week 4 |
Round 1: SP Jameson Taillon - ChN Round 2: 3B Maikel Garcia - KC |
Round 1: 3B Anthony Rendon - LAA Round 2: 3B D.J. LeMahieu - NYA |
| Week 5 |
Round 2: C Patrick Bailey - SF |
Round 2: C Henry Davis - Pit |
| Week 6 |
Round 1: OF Wenceel Perez - Det |
Round 1: OF Sal Frelick - Mil Round 2: SP Dane Dunning - Tex |
| 1st Team | 2nd Team |
| Pre-Season | |
| Cubs Win | Poker in the Rear |
|
OF
Randy Arozarena
TB |
Round 3, 9th Pick (SP Tanner Bibee Cle) |
| Pre-Season | |
| Cubs Win | Bat Crack Fever |
|
OF
Ian Happ
ChN |
Round 6, 2nd Pick (1B Anthony Rizzo NYA) |
| Pre-Season | |
| Cubs Win | Popcorn Obliques |
|
SP
Logan Gilbert
Sea |
Round 6, 6th Pick (C Willson Contreras StL) |
| Pre-Season | |
| Cubs Win | Bleacher Bums |
|
Round 4, 12th Pick (SP Mitch Keller Pit) |
C
Luis Campusano
SD |
| Pre-Season | |
| Cubs Win | Popcorn Obliques |
|
Round 3, 12th Pick (OF Giancarlo Stanton NYA) |
Round 12, 6th Pick (2B Thairo Estrada SF) |
| Pre-Season | |
| Cubs Win | Bat Crack Fever |
|
Round 2, 12th Pick (2B Xander Bogaerts SD) |
SP
Kyle Harrison
SF |
| Pre-Season | |
| Cubs Win | Fight at the Bat Rack |
|
3B
Isaac Paredes
TB |
Round 4, 1st Pick (SS Carlos Correa Min) |
| Week 3 | |
| Cubs Win | Popcorn Obliques |
|
SS
Carlos Correa
Min |
OF
Sal Frelick
Mil 1B Christian Encarnacion-Strand Cin |