| Week | Add | Drop |
| Pre-Season |
Round A: OF Evan Carter - Tex | |
| Week 1 |
Round 2: SP Brady Singer - KC | |
| Week 2 |
Round 1: C Joey Bart - Pit Round 2: OF Micahel Taylor - Pit | |
| Week 3 |
Round 1: SP Trevor Williams - Was Round 2: SS Masyn Winn - StL |
Round 1: OF Micahel Taylor - Pit Round 2: SP Trevor Williams - Was |
| Week 4 |
Round 1: OF Jake Fraley - Cin |
Round 1: C Joey Bart - F/A |
| Week 5 |
Round 2: SP Jose Quintana - NYN |
| 1st Team | 2nd Team |
| Pre-Season | |
| ChiSox28 | Dallas Cubans |
|
OF
Julio Rodriguez
Sea Round 6, 2nd Pick (OF James Outman LAD) |
OF
Eloy Jimenez
ChA C Will Smith LAD OF Adolis Garcia Tex SS Anthony Volpe NYA 3B Curtis Mead TB |
| Pre-Season | |
| ChiSox28 | Dallas Cubans |
|
Round 12, 2nd Pick (1B Nolan Schanuel LAA) |
Round 15, 1st Pick (OF Lourdes Gurriel Ari) Round 16, 1st Pick (OF Sal Frelick Mil) Round 15, 11th Pick (SP Frankie Montas Cin) Round 16, 11th Pick |
| Pre-Season | |
| ChiSox28 | Dallas Cubans |
|
C
Will Smith
LAD OF Jackson Chourio Mil |
C
Willson Contreras
StL 3B Ryan McMahon Col 1B Nolan Schanuel LAA SS Jackson Merrill SD |
| Pre-Season | |
| ChiSox28 | Al Davis Hombres |
|
OF
Sal Frelick
Mil |
RP
Craig Kimbrel
Bal |
| Pre-Season | |
| ChiSox28 | Dallas Cubans |
|
2B
Brandon Drury
LAA OF Evan Carter Tex |
2B
Matt McLain
Cin OF Jung Hoo Lee SF |
| Pre-Season | |
| ChiSox28 | That's What She Said |
|
OF
Spencer Steer
Cin |
Round 3, 10th Pick (3B Jake Burger Mia) |
| Pre-Season | |
| ChiSox28 | Dallas Cubans |
|
2B
Matt McLain
Cin Round 2, 2nd Pick (RP Andres Munoz Sea) |
SP
Tyler Glasnow
LAD 3B Royce Lewis Min |
| Pre-Season | |
| ChiSox28 | Cleveland Tate Stars |
|
OF
Dylan Crews
Was |
Round 6, 5th Pick (SP Jose Berrios Tor) |
| Pre-Season | |
| ChiSox28 | Rays |
|
C
Endy Rodriguez
Pit |
Round 2, 12th Pick (RP Clay Holmes NYA) Round 6, 12th Pick (SP Yu Darvish SD) |
| Pre-Season | |
| ChiSox28 | Rene Baum |
|
OF
Seiya Suzuki
ChN |
1B
Yandy Diaz
TB |
| Pre-Season | |
| ChiSox28 | Whiz Kids |
|
SP
Bobby Miller
LAD Round 19, 2nd Pick (SP Garrett Crochet ChA) |
Round 3, 9th Pick (1B Ryan Mountcastle Bal) |
| Pre-Season | |
| ChiSox28 | Dallas Cubans |
|
SP
Eury Perez
Mia Round 5, 2nd Pick (SP Merrill Kelly Ari) |
RP
Camilo Doval
SF OF Heston Kjerstad Bal |
| Week 1 | |
| ChiSox28 | Al Davis Hombres |
|
OF
Jorge Soler
SF SP Zach Eflin TB 3B Jake Burger Mia |
OF
Nick Castellanos
Phi SP Ryan Pepiot TB 1B Vinnie Pasquantino KC |
| Week 3 | |
| ChiSox28 | Dallas Cubans |
|
RP
Clay Holmes
NYA SS Anthony Volpe NYA |
SS
Carlos Correa
Min OF Will Benson Cin |
| Week 5 | |
| ChiSox28 | Al Davis Hombres |
|
3B
Royce Lewis
Min 2B Matt McLain Cin 1B Vinnie Pasquantino KC |
2B
Jose Altuve
Hou OF Jorge Soler SF SP Max Fried Atl C Jonah Heim Tex SP Cristopher Sanchez Phi |
| Week 5 | |
| ChiSox28 | Dallas Cubans |
|
C
Will Smith
LAD |
SP
Marcus Stroman
NYA C Sean Murphy Atl |