| Week | Add | Drop |
| Pre-Season |
Round 1: SP Andrew Heaney - Tex Round 2: SP Kyle Freeland - Col Round A: SS Gavin Lux - LAD Round B: SP Ricky Tiedemann - Tor |
Round 1: C Gary Sanchez - Mil Round A: C Endy Rodriguez - Pit Round B: C Tyler Stephenson - Cin |
| Week 1 |
Round 1: SP Brady Singer - KC Round 2: C Carson Kelly - Det | |
| Week 2 |
Round 1: SP Yariel Rodriguez - Tor Round 2: SP Spencer Turnbull - Phi |
Round 1: SP Kyle Freeland - Col Round 2: SP Andrew Heaney - Tex |
| Week 3 |
Round 1: OF Joey Loperfido - Hou Round 2: SP Mike Lorenzen - Tex |
Round 1: 3B Yoan Moncada - ChA Round 2: RP Jose Leclerc - Tex |
| Week 4 |
Round 1: RP Kirby Yates - Tex Round 2: 1B Bobby Dalbec - Bos |
Round 1: 1B Kris Bryant - Col Round 2: SP Spencer Turnbull - Phi |
| Week 5 |
Round 1: C Patrick Bailey - SF Round 2: 1B Ty France - Sea |
Round 1: C Carson Kelly - Det Round 2: OF Jose Siri - TB |
| Week 6 |
Round 1: SP Jack Flaherty - Det Round 2: OF Tommy Pham - ChA |
Round 1: 1B Bobby Dalbec - Bos Round 2: OF Masataka Yoshida - Bos |
| Week 7 |
Round 1: OF Mike Tauchman - ChN Round 2: SP Clayton Kershaw - LAD |
Round 1: SP Gavin Williams - Cle Round 2: SP Jack Flaherty - Det |
| 1st Team | 2nd Team |
| Pre-Season | |
| Mo Money Mo Problems | Marlins |
|
3B
Royce Lewis
Min |
Round 2, 8th Pick (SP Brayan Bello Bos) |
| Pre-Season | |
| Mo Money Mo Problems | PHILLIE PRIDE |
|
Round 4, 9th Pick (1B Andrew Vaughn ChA) |
1B
Ryan O'Hearn
Bal |
| Pre-Season | |
| Mo Money Mo Problems | Lansing Lugnuts |
|
OF
Byron Buxton
Min OF Bryan Reynolds Pit SP Shane McClanahan TB |
Round 2, 3rd Pick (OF Teoscar Hernández LAD) Round 5, 3rd Pick (RP Paul Sewald Ari) |
| Week 5 | |
| Mo Money Mo Problems | Dream Machine |
|
OF
Chase DeLauter
Cle SP Yariel Rodriguez Tor |
1B
Anthony Rizzo
NYA OF Adam Duvall Atl |
| Week 7 | |
| Mo Money Mo Problems | San Diego Tigers |
|
OF
Joey Loperfido
Hou |
C
Luis Campusano
SD |