| Week | Add | Drop |
| Week 1 |
Round 1: OF Victor Scott - StL Round 2: SS Isiah Kiner-Falefa - Pit Round 3: 3B Ernie Clement - Tor | |
| Week 2 |
Round 1: OF Gavin Sheets - SD Round 2: SP Martin Perez - ChA Round 3: SP Chad Patrick - Mil |
Round 1: RP Ryne Nelson - Ari Round 2: OF Bryan De La Cruz - Atl Round 3: 3B Ernie Clement - Tor |
| Week 3 |
Round 1: 3B Dylan Moore - Sea Round 3: OF Zac Veen - Col |
Round 1: RP Chris Martin - Tex Round 3: OF Gavin Sheets - SD |
| Week 4 |
Round 1: RP Emilio Pagan - Cin Round 3: OF Chandler Simpson - TB |
Round 1: OF Jake McCarthy - Ari Round 3: SS Isiah Kiner-Falefa - Pit |
| Week 5 |
Round 1: 1B Nick Kurtz - Oak Round 2: 1B Eric Wagaman - Mia Round 3: RP Will Vest - Det |
Round 3: 1B Colt Keith - Det |
| Week 6 |
Round 2: SS Javier Baez - Det Round 3: SP Lance McCullers - Hou |
Round 2: SP Martin Perez - ChA Round 3: RP Will Vest - Det |
| Week 7 |
Round 3: 3B Brett Baty - NYN |
Round 3: SP Lance McCullers - Hou |
| Week 9 |
Round 2: 1B Triston Casas - Bos Round 3: OF Jerar Encarnación - SF |
Round 2: 1B Eric Wagaman - Mia Round 3: C Jonah Heim - Tex |
| Week 10 |
Round 3: SP Lance McCullers - Hou |
Round 3: 3B Brett Baty - NYN |
| Week 11 |
Round 2: SP Mick Abel - Phi Round 3: 1B Jac Caglianone - KC |
Round 2: SP Tyler Anderson - LAA Round 3: SS Javier Baez - Det |
| Week 12 |
Round 1: SP Bryce Elder - Atl Round 3: SS Leodalis De Vries - SD |
Round 1: OF Chandler Simpson - TB Round 3: OF Christopher Morel - TB |
| Week 13 |
Round 3: SP AJ Smith-Shawver - Atl |
Round 3: 3B Dylan Moore - Sea |
| Week 15 |
Round 3: 1B Jake Burger - Tex |
| 1st Team | 2nd Team |
| Pre-Season | |
| Wrigley Bleacher Bums | kOZZIE BALL |
|
Round 6, 7th Pick (RP Jeff Hoffman Tor) |
C
Salvador Perez
KC |
| Pre-Season | |
| Wrigley Bleacher Bums | Vegas Green and Gold |
|
Round 4, 7th Pick (RP AJ Puk Ari) |
3B
Royce Lewis
Min |
| Pre-Season | |
| Wrigley Bleacher Bums | Yankee Pride |
|
OF
Kyle Schwarber
Phi Round 5, 7th Pick (3B Ryan McMahon Col) |
OF
Luis Robert Jr.
ChA SP Tanner Bibee Cle Round 7, 9th Pick (2B Bryson Stott Phi) |
| Pre-Season | |
| Wrigley Bleacher Bums | 1 Rockin Redbirds |
|
3B
Manny Machado
SD Round 2, 7th Pick (SP Freddy Peralta Mil) |
SP
Sonny Gray
StL SS Willy Adames SF SP Justin Steele ChN |
| Pre-Season | |
| Wrigley Bleacher Bums | Vegas Green and Gold |
|
Round 1, 7th Pick (RP Mason Miller Oak) Round 3, 7th Pick (1B Jonathan Aranda TB) |
SP
Chris Sale
Atl SP Pablo Lopez Min |
| Pre-Season | |
| Wrigley Bleacher Bums | Yankee Pride |
|
3B
Austin Riley
Atl |
SP
George Kirby
Sea RP Felix Bautista Bal |
| Pre-Season | |
| Wrigley Bleacher Bums | 1 Rockin Redbirds |
|
OF
Teoscar Hernández
LAD SP Pablo Lopez Min |
DH
Marcell Ozuna
Atl Round 17, 12th Pick (RP Ryne Nelson Ari) Round 18, 12th Pick (OF Christopher Morel TB) Round 19, 12th Pick |
| Pre-Season | |
| Wrigley Bleacher Bums | Chiraq Villains |
|
2B
Brandon Lowe
TB |
Round 7, 1st Pick (1B Colt Keith Det) |
| Pre-Season | |
| Wrigley Bleacher Bums | Orvon 26 |
|
OF
Luis Robert Jr.
ChA |
Round 2, 3rd Pick (OF Roman Anthony Bos) |
| Week 12 | |
| Wrigley Bleacher Bums | 1 Rockin Redbirds |
|
SP
Sonny Gray
StL SS Willy Adames SF SP Bailey Ober Min |
SP
Justin Verlander
SF SS Jeremy Pena Hou SP Brandon Pfaadt Ari |
| Week 13 | |
| Wrigley Bleacher Bums | 1 Rockin Redbirds |
|
RP
Felix Bautista
Bal |
OF
Giancarlo Stanton
NYA |