| Week | Add | Drop |
| Pre-Season |
Round 1: OF Jose Siri - TB Round 2: OF Victor Scott - StL Round A: SS Gavin Lux - LAD Round B: SP Ricky Tiedemann - Tor |
Round 2: OF Jose Siri - TB Round A: SP Zack Littell - TB Round B: OF Chris Taylor - LAD |
| Week 1 |
Round 1: SP Jordan Hicks - SF Round 2: SP James Paxton - Bos | |
| Week 2 |
Round 1: SP Yariel Rodriguez - Tor Round 2: OF Joey Gallo - Was |
Round 1: OF Victor Scott - StL Round 2: 1B Jose Abreu - Hou |
| Week 3 |
Round 1: OF Joey Loperfido - Tor Round 2: 1B Kyle Manzardo - Cle |
Round 1: 3B D.J. LeMahieu - NYA Round 2: SP Hunter Greene - Cin |
| Week 4 |
Round 1: 1B Ryan O'Hearn - Bal Round 2: OF Bryan De La Cruz - Pit |
Round 1: SS Brayan Rocchio - Cle Round 2: 1B Andrew Vaughn - ChA |
| Week 5 |
Round 1: RP José Soriano - LAA Round 2: SS Amed Rosario - LAD |
Round 1: SP Yariel Rodriguez - Tor Round 2: OF Jarred Kelenic - Atl Round 2: OF Joey Gallo - Was |
| Week 6 |
Round 1: OF Tommy Pham - StL Round 2: 3B Nick Senzel - ChA |
Round 2: OF Masataka Yoshida - Bos |
| Week 7 |
Round 1: 3B Brett Harris - Oak Round 2: SP Clayton Kershaw - LAD |
Round 1: RP José Soriano - LAA Round 2: SP Max Meyer - Mia |
| Week 8 |
Round 1: OF Lazaro Montes - Sea Round 2: SS Marco Luciano - SF |
Round 1: 3B Brett Harris - Oak Round 2: 3B Brett Baty - NYN |
| Week 9 |
Round 1: 2B Michael Massey - KC Round 1: 2B Michael Massey - KC Round 2: 2B Jorge Mateo - Bal |
Round 1: SS Amed Rosario - Cin Round 1: SS Amed Rosario - Cin Round 2: 2B Michael Massey - KC |
| Week 10 |
Round 1: OF Nelson Velazquez - KC Round 2: C Keibert Ruiz - Was |
Round 1: 2B Jorge Mateo - Bal Round 2: C Gabriel Moreno - Ari Round 2: SS Marco Luciano - SF |
| Week 11 |
Round 1: 2B Michael Massey - KC Round 2: 2B Rob Refsnyder - Bos |
Round 2: 2B Brendan Rodgers - Col |
| Week 12 |
Round 1: SS David Hamilton - Bos Round 2: OF Max Kepler - Min |
Round 1: 2B Rob Refsnyder - Bos Round 2: OF Cedric Mullins II - Bal Round 2: DH Justin Turner - Sea |
| Week 13 |
Round 1: SP Spencer Turnbull - Phi Round 2: OF Jarred Kelenic - Atl |
Round 1: OF Nelson Velazquez - KC Round 2: OF Max Kepler - Min |
| Week 14 |
Round 1: RP Felix Bautista - Bal Round 2: OF Alek Thomas - Ari |
Round 1: SP Spencer Turnbull - Phi |
| Week 15 |
Round 1: SP DJ Herz - Was Round 2: SP Yariel Rodriguez - Tor |
Round 1: 3B Nick Senzel - ChA Round 2: SP Jordan Hicks - SF |
| Week 16 |
Round 1: SP Spencer Schwellenbach - Atl Round 2: SP Tyler Phillips - Phi |
Round 2: SP Yariel Rodriguez - Tor |
| Week 17 |
Round 2: SP DJ Herz - Was | |
| Week 18 |
Round 1: OF Tyler Fitzgerald - SF Round 2: OF Cedric Mullins II - Bal |
Round 1: SP James Paxton - Bos Round 2: SS David Hamilton - Bos |
| Week 19 |
Round 1: SS Marco Luciano - SF Round 2: SP Trevor Rogers - Bal |
Round 1: OF Jarred Kelenic - Atl Round 2: SP Tyler Phillips - Phi |
| Week 20 |
Round 1: SP Eduardo Rodriguez - Ari Round 2: RP Ryan Walker - SF |
Round 1: SS Marco Luciano - SF Round 2: RP Camilo Doval - SF |
| Week 22 |
Round 1: OF Kristian Campbell - Bos Round 2: SP Sandy Alcantara - Mia |
Round 2: SP Trevor Rogers - Bal Round 2: OF Alek Thomas - Ari Round 2: SP Eduardo Rodriguez - Ari |
| 1st Team | 2nd Team |
| Pre-Season | |
| Mo Money Mo Problems | The Shogun of Harlem |
|
C
Gabriel Moreno
Ari |
|
| Pre-Season | |
| Mo Money Mo Problems | The Plantation |
|
SS
Trevor Story
Bos 2B Colt Keith Det |
|
| Pre-Season | |
| Mo Money Mo Problems | Enid Harvesters |
|
1B
Anthony Rizzo
NYA OF Josh Lowe TB |
|
| Week 10 | |
| Mo Money Mo Problems | Enid Harvesters |
|
SP
Shane McClanahan
TB RP Alexis Diaz Cin SS Jackson Holliday Bal OF Lazaro Montes Sea 1B Kyle Manzardo Cle OF Joey Loperfido Tor |
OF
Jorge Soler
SF 2B Brendan Rodgers Col SS Dansby Swanson ChN 2B Willi Castro Min SP Kutter Crawford Bos RP Emmanuel Clase Cle |
| Week 12 | |
| Mo Money Mo Problems | The Plantation |
|
OF
Tommy Pham
ChA Round 1, 10th Pick (SP Bryce Miller Sea) Round 3, 10th Pick (SP Carlos Rodon NYA) |
OF
Cody Bellinger
ChN |
| Week 14 | |
| Mo Money Mo Problems | The Plantation |
|
SP
Kutter Crawford
Bos SP Brayan Bello Bos Round 2, 10th Pick (SP Bryan Woo Sea) Round 4, 10th Pick (3B Eugenio Suarez Ari) |
SP
Cole Ragans
KC SP Cristopher Sanchez Phi |