| 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 - LAD | |
| 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 - Hou 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 - Mia |
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 - TB |
Round 1: SP Yariel Rodriguez - Tor Round 2: OF Joey Gallo - Was Round 2: OF Jarred Kelenic - Atl |
| Week 6 |
Round 1: OF Tommy Pham - ChA Round 2: 3B Nick Senzel - Was |
Round 2: OF Masataka Yoshida - Bos |
| 1st Team | 2nd Team |
| Pre-Season | |
| Mo Money Mo Problems | Florence Y’alls |
|
SS
Trevor Story
Bos 2B Colt Keith Det |
Round 6, 7th Pick (SP Bryce Miller Sea) |
| Pre-Season | |
| Mo Money Mo Problems | Enid Harvesters |
|
1B
Anthony Rizzo
NYA OF Josh Lowe TB |
Round 3, 5th Pick (RP Alexis Diaz Cin) Round 6, 5th Pick (1B Andrew Vaughn ChA) |
| Pre-Season | |
| Mo Money Mo Problems | The Shogun of Harlem |
|
Round 4, 12th Pick (C Logan O'Hoppe LAA) |
C
Gabriel Moreno
Ari |