| Week | Add | Drop |
| Pre-Season |
Round 1: SP Clarke Schmidt - NYA Round A: SP Brandon Pfaadt - Ari Round B: OF Jung Hoo Lee - SF |
Round 1: OF Roman Anthony - Bos Round A: 2B Miguel Vargas - LAD |
| Week 1 |
Round 2: SP Tanner Houck - Bos | |
| Week 2 |
Round 1: 3B Jared Triolo - Pit Round 2: OF JJ Bleday - Oak | |
| Week 3 |
Round 1: 2B Vaughn Grissom - Bos Round 2: SP José Butto - NYN |
Round 1: SP Tyler Wells - Bal Round 2: SS Trevor Story - Bos |
| Week 4 |
Round 1: OF Jurickson Profar - SD Round 2: 3B Patrick Wisdom - ChN |
Round 1: OF JJ Bleday - Oak Round 2: 3B J.D. Davis - Oak |
| Week 5 |
Round 1: C Joey Bart - Pit Round 2: 2B Brendan Rodgers - Col |
Round 1: 3B Jared Triolo - Pit Round 2: SP José Butto - NYN |
| Week 6 |
Round 1: SP Jack Flaherty - Det Round 2: OF Max Kepler - Min |
Round 1: OF James Outman - LAD Round 2: 2B Brendan Rodgers - Col |
| Week 7 |
Round 1: SP Erick Fedde - ChA Round 2: OF Trevor Larnach - Min |
Round 1: C Francisco Álvarez - NYN Round 2: SP Jack Flaherty - Det |
| 1st Team | 2nd Team |
| Pre-Season | |
| Jacksonville Red Caps | Built 4 Speed |
|
Round 5, 3rd Pick (SS Ezequiel Tovar Col) |
RP
Josh Hader
Hou |
| Pre-Season | |
| Jacksonville Red Caps | Sons of Pitches |
|
C
Gary Sanchez
Mil |
Round 1, 9th Pick (1B Josh Naylor Cle) Round 5, 9th Pick (RP Ryan Helsley StL) Round 6, 9th Pick (2B Brandon Lowe TB) |
| Pre-Season | |
| Jacksonville Red Caps | Bedlam at the Bank |
|
Round 3, 3rd Pick (3B Alec Bohm Phi) |
C
Francisco Álvarez
NYN |
| Week 2 | |
| Jacksonville Red Caps | Long Island Margaritaville |
|
SP
Dylan Cease
SD |
SS
C.J. Abrams
Was |