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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Grant Holmes# | 15 | 2020-2020 | |
| 2 | Alex Faedo# | 13 | 2020-2020 | |
| 2 | Rony Garcia# | 13 | 2020-2020 | |
| 4 | Adbert Alzolay# | 12 | 2020-2020 | |
| 4 | Brett Conine# | 12 | 2020-2020 | |
| 4 | Sean Hjelle# | 12 | 2020-2020 | |
| 4 | Thomas Pannone# | 12 | 2020-2020 | |
| 4 | Tommy Parsons# | 12 | 2020-2020 | |
| 4 | David Peterson# | 12 | 2020-2020 | |
| 4 | Cristopher Sanchez# | 12 | 2020-2020 | |
| 11 | Yency Almonte# | 11 | 2020-2020 | |
| 11 | James Kaprielian# | 11 | 2020-2020 | |
| 11 | Jack Patterson# | 11 | 2020-2020 | |
| 11 | Yefry Ramirez# | 11 | 2020-2020 | |
| 15 | Shaun Anderson# | 10 | 2020-2020 | |
| 15 | Wil Crowe# | 10 | 2020-2020 | |
| 15 | Josh Green# | 10 | 2020-2020 | |
| 15 | Nick Lodolo# | 10 | 2020-2020 | |
| 15 | Jorge Lopez# | 10 | 2020-2020 | |
| 15 | Shane McClanahan# | 10 | 2020-2020 | |
| 15 | Adrian Morejon# | 10 | 2020-2020 | |
| 15 | Kyle Muller# | 10 | 2020-2020 | |
| 15 | Matt Peacock# | 10 | 2020-2020 | |
| 15 | Sean Reid-Foley# | 10 | 2020-2020 | |
| 15 | Tarik Skubal# | 10 | 2020-2020 | |
| 15 | Brandon Waddell# | 10 | 2020-2020 | |
| 15 | Jake Woodford# | 10 | 2020-2020 | |
| 15 | Huascar Ynoa# | 10 | 2020-2020 | |
| 29 | Cory Abbott# | 9 | 2020-2020 | |
| 29 | Brandon Bielak# | 9 | 2020-2020 | |
| 29 | Justin Dunn# | 9 | 2020-2020 | |
| 29 | Derian Gonzalez# | 9 | 2020-2020 | |
| 29 | Joe Palumbo# | 9 | 2020-2020 | |
| 29 | Jared Robinson# | 9 | 2020-2020 | |
| 29 | Keyvius Sampson# | 9 | 2020-2020 | |
| 29 | Devan Watts# | 9 | 2020-2020 | |
| 29 | Mitchell White# | 9 | 2020-2020 | |
| 38 | Cody Bolton# | 8 | 2020-2020 | |
| 38 | Steven Brault# | 8 | 2020-2020 | |
| 38 | Genesis Cabrera# | 8 | 2020-2020 | |
| 38 | Aaron Civale# | 8 | 2020-2020 | |
| 38 | Jasseel De La Cruz# | 8 | 2020-2020 | |
| 38 | Mike Leake# | 8 | 2020-2020 | |
| 38 | Sam McWilliams# | 8 | 2020-2020 | |
| 38 | Tyson Miller# | 8 | 2020-2020 | |
| 38 | Jordan Montgomery# | 8 | 2020-2020 | |
| 38 | Mike Montgomery# | 8 | 2020-2020 | |
| 38 | Nick Nelson# | 8 | 2020-2020 | |
| 38 | Sean Newcomb# | 8 | 2020-2020 | |
| 38 | David Parkinson# | 8 | 2020-2020 | |
| 38 | Williams Perez# | 8 | 2020-2020 | |
| 38 | Cody Ponce# | 8 | 2020-2020 | |
| 38 | Ryan Rolison# | 8 | 2020-2020 | |
| 38 | Patrick Sandoval# | 8 | 2020-2020 | |
| 38 | John Schreiber# | 8 | 2020-2020 | |
| 38 | Shawn Semple# | 8 | 2020-2020 | |
| 38 | Chris Stratton# | 8 | 2020-2020 | |
| 38 | Keegan Thompson# | 8 | 2020-2020 | |
| 38 | Trent Thornton# | 8 | 2020-2020 | |
| 60 | Silvino Bracho# | 7 | 2020-2020 | |
| 60 | Yennsy Diaz# | 7 | 2020-2020 | |
| 60 | Robert Dugger# | 7 | 2020-2020 | |
| 60 | Parker Dunshee# | 7 | 2020-2020 | |
| 60 | Jon Duplantier# | 7 | 2020-2020 | |
| 60 | Zach Eflin# | 7 | 2020-2020 | |
| 60 | Josh Fleming# | 7 | 2020-2020 | |
| 60 | Julian Garcia# | 7 | 2020-2020 | |
| 60 | Josiah Gray# | 7 | 2020-2020 | |
| 60 | Spencer Howard# | 7 | 2020-2020 | |
| 60 | Brett Kennedy# | 7 | 2020-2020 | |
| 60 | Dustin May# | 7 | 2020-2020 | |
| 60 | Cionel Perez# | 7 | 2020-2020 | |
| 60 | Bruce Rondon# | 7 | 2020-2020 | |
| 60 | Brady Singer# | 7 | 2020-2020 | |
| 60 | Bennett Sousa# | 7 | 2020-2020 | |
| 60 | Trevor Stephan# | 7 | 2020-2020 | |
| 60 | Thomas Szapucki# | 7 | 2020-2020 | |
| 78 | Jorge Alcala# | 6 | 2020-2020 | |
| 78 | Brett Anderson# | 6 | 2020-2020 | |
| 78 | Rogelio Armenteros# | 6 | 2020-2020 | |
| 78 | Jaime Barria# | 6 | 2020-2020 | |
| 78 | Paul Campbell# | 6 | 2020-2020 | |
| 78 | Yeizo Campos# | 6 | 2020-2020 | |
| 78 | Jesus Castillo# | 6 | 2020-2020 | |
| 78 | Jose Castillo# | 6 | 2020-2020 | |
| 78 | Luis Cessa# | 6 | 2020-2020 | |
| 78 | Dane Dunning# | 6 | 2020-2020 | |
| 78 | Matt Foster# | 6 | 2020-2020 | |
| 78 | Enderson Franco# | 6 | 2020-2020 | |
| 78 | Joey Gerber# | 6 | 2020-2020 | |
| 78 | Chi Chi Gonzalez# | 6 | 2020-2020 | |
| 78 | Ashton Goudeau# | 6 | 2020-2020 | |
| 78 | Blaine Hardy# | 6 | 2020-2020 | |
| 78 | Codi Heuer# | 6 | 2020-2020 | |
| 78 | Bryan Hudson# | 6 | 2020-2020 | |
| 78 | Cristian Javier# | 6 | 2020-2020 | |
| 78 | Anthony Kay# | 6 | 2020-2020 | |
| 78 | Michael Kopech# | 6 | 2020-2020 | |
| 78 | Matt Krook# | 6 | 2020-2020 | |
| 78 | Asa Lacy# | 6 | 2020-2020 |
