| Week | Add | Drop |
| Pre-Season |
Round 1: RP Kevin Ginkel - Ari Round A: SP Ryan Pepiot - TB |
Round A: OF Adam Duvall - Atl |
| Week 1 |
Round 1: SP Brady Singer - KC Round 2: 1B Jared Walsh - ChA |
Round 1: SS Wander Franco - TB Round 2: 3B Anthony Rendon - LAA |
| Week 3 |
Round 1: OF Edward Olivares - Pit Round 2: OF Brenton Doyle - Col |
Round 1: C Keibert Ruiz - Was Round 2: 1B Jared Walsh - ChA |
| Week 4 |
Round 1: OF Andy Pages - LAD Round 2: SS Amed Rosario - TB |
Round 1: OF Brenton Doyle - Col Round 2: OF Edward Olivares - Pit |
| Week 5 |
Round 1: OF Trevor Larnach - Min Round 2: 3B Mark Vientos - NYN |
Round 2: 1B Kris Bryant - Col |
| Week 6 |
Round 1: C Danny Jansen - Tor Round 2: 2B Luis Rengifo - LAA |
Round 2: SP Brandon Pfaadt - Ari |
| 1st Team | 2nd Team |
| Pre-Season | |
| NYSE: CTAS | Koshkonong |
|
Round 6, 7th Pick (OF Masataka Yoshida Bos) |
OF
Eloy Jimenez
ChA |
| Pre-Season | |
| NYSE: CTAS | D & D |
|
OF
Eloy Jimenez
ChA |
Round 5, 3rd Pick (2B Edouard Julien Min) |
| Pre-Season | |
| NYSE: CTAS | Chaos Creators |
|
C
Endy Rodriguez
Pit |
Round 1, 5th Pick (SP Bobby Miller LAD) Round 6, 5th Pick (SP Ryan Pepiot TB) |
| Pre-Season | |
| NYSE: CTAS | TARLINI CHECK DOWN |
|
C
Tyler Soderstrom
Oak |
Round 1, 9th Pick (OF Riley Greene Det) |
| Pre-Season | |
| NYSE: CTAS | Single Malt Drinkin' |
|
SP
Kyle Harrison
SF |
Round 3, 10th Pick (DH J.D. Martinez NYN) |
| Pre-Season | |
| NYSE: CTAS | D & D |
|
Round 15, 7th Pick (1B Ryan Noda Oak) Round 16, 7th Pick (SP James Paxton LAD) Round 17, 7th Pick (C Travis d'Arnaud Atl) Round 18, 7th Pick (OF Jose Siri TB) Round 19, 7th Pick (3B Ezequiel Duran Tex) |
Round 12, 3rd Pick (1B Kris Bryant Col) |