| Week | Add | Drop |
| Pre-Season |
Round 1: RP Kevin Ginkel - Ari Round A: SP Yoshinobu Yamamoto - LAD |
Round 1: OF Daulton Varsho - Tor |
| Week 1 |
Round 1: OF Michael Conforto - SF Round 2: 3B Ezequiel Duran - Tex | |
| Week 2 |
Round 1: SS Oswaldo Cabrera - NYA Round 2: RP James McArthur - KC |
Round 1: 3B Ezequiel Duran - Tex Round 2: RP Kevin Ginkel - Ari |
| Week 3 |
Round 1: OF Joey Loperfido - Hou |
Round 1: 2B Brendan Rodgers - Col |
| Week 4 |
Round 1: RP Kirby Yates - Tex Round 2: 1B Bobby Dalbec - Bos |
Round 1: 1B Kris Bryant - Col Round 2: SP Yu Darvish - SD |
| Week 5 |
Round 1: 1B Joey Meneses - Was Round 2: 2B Rob Refsnyder - Bos |
Round 1: 1B Bobby Dalbec - Bos Round 2: RP Jhoan Duran - Min |
| Week 6 |
Round 1: 3B Tyler Black - Mil Round 2: 2B Michael Massey - KC |
Round 1: 2B Colt Keith - Det Round 2: OF Chase DeLauter - Cle |
| Week 7 |
Round 1: SP Taj Bradley - TB Round 2: C Francisco Álvarez - NYN |
Round 1: 2B Rob Refsnyder - Bos Round 2: SP Marcus Stroman - NYA |
| 1st Team | 2nd Team |
| Pre-Season | |
| Bedlam at the Bank | NYSE: DLR |
|
OF
Jazz Chisholm
Mia Round 3, 1st Pick (RP David Bednar Pit) |
OF
Byron Buxton
Min OF Eloy Jimenez ChA |
| Pre-Season | |
| Bedlam at the Bank | Brooklyn Cyclones III |
|
SP
Tanner Bibee
Cle |
Round 4, 2nd Pick (SP Walker Buehler LAD) |
| Pre-Season | |
| Bedlam at the Bank | Jacksonville Red Caps |
|
C
Francisco Álvarez
NYN |
Round 3, 3rd Pick (3B Alec Bohm Phi) |
| Week 2 | |
| Bedlam at the Bank | Long Island Margaritaville |
|
SP
Bryce Miller
Sea |
OF
Jarren Duran
Bos |
| Week 5 | |
| Bedlam at the Bank | Sons of Pitches |
|
RP
Robert Suarez
SD |
1B
Anthony Rizzo
NYA |