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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Zak Kent | 65 | 2021-2027 | |
| 2 | Leury Tejada# | 39 | 2022-2026 | |
| 3 | Jayden Murray | 35 | 2022-2024 | |
| 3 | Ricky Vanasco# | 35 | 2019-2025 | |
| 5 | Anton Carrillo# | 34 | 2025-2029 | |
| 6 | Rich Delgado# | 33 | 2026-2029 | |
| 6 | Wilber Perez | 33 | 2019-2023 | |
| 8 | Enmanuel De Jesus | 32 | 2016-2022 | |
| 8 | Mason Englert | 32 | 2023-2027 | |
| 8 | Drew Rom# | 32 | 2019-2024 | |
| 8 | Josh Shedd# | 32 | 2027-2029 | |
| 8 | Mike Shope# | 32 | 2025-2029 | |
| 8 | Chih-Ting Wang | 32 | 2021-2025 | |
| 14 | Jose Miguel Gonzalez | 31 | 2022-2025 | |
| 14 | Tyler Owens# | 31 | 2021-2024 | |
| 16 | Ronni Montero# | 30 | 2021-2028 | |
| 17 | Eric Hall# | 27 | 2025-2029 | |
| 17 | Shusake Kato | 27 | 2022-2027 | |
| 17 | Alex Scherff | 27 | 2018-2024 | |
| 17 | Tom Zwicker# | 27 | 2022-2027 | |
| 21 | Chris Murphy | 26 | 2021-2024 | |
| 21 | Sergio Pacheco | 26 | 2019-2027 | |
| 21 | Josh Paine# | 26 | 2026-2027 | |
| 24 | Ron Allred# | 25 | 2027-2029 | |
| 24 | Will Kincanon | 25 | 2018-2023 | |
| 24 | Mike Rathwell# | 25 | 2023-2025 | |
| 24 | Andres Rivero# | 25 | 2028-2029 | |
| 24 | Lenny Torres# | 25 | 2021-2023 | |
| 29 | Ken Hanson# | 24 | 2026-2029 | |
| 29 | Bernardo Hiraldo | 24 | 2023-2027 | |
| 29 | Yusniel Padron-Artilles# | 24 | 2019-2023 | |
| 29 | Omar Perez# | 24 | 2026-2029 | |
| 33 | Jerry Adhami | 23 | 2025-2026 | |
| 33 | Luis Enrique Cedeno | 23 | 2015-2018 | |
| 33 | Johan Dominguez | 23 | 2019-2023 | |
| 36 | Jason Bilous | 22 | 2019-2023 | |
| 36 | Logan Boyd | 22 | 2016-2017 | |
| 36 | Jeronimo Castro# | 22 | 2021-2025 | |
| 36 | Josh Dye | 22 | 2019-2024 | |
| 36 | Kymani Fuller | 22 | 2022-2028 | |
| 36 | Joe Levins | 22 | 2024-2025 | |
| 36 | Danny Olson# | 22 | 2022-2024 | |
| 36 | Kade Strowd | 22 | 2022-2024 | |
| 36 | Carlos Velez | 22 | 2024-2025 | |
| 45 | Tristen Chatman# | 21 | 2025-2027 | |
| 45 | Eli Curtis# | 21 | 2025-2029 | |
| 45 | Garrett Davila | 21 | 2017-2022 | |
| 45 | Armando Furuta# | 21 | 2028-2029 | |
| 45 | Jesus Guardanapos# | 21 | 2026-2029 | |
| 45 | Phil Hill# | 21 | 2028-2029 | |
| 45 | Blaine Knight | 21 | 2019-2024 | |
| 45 | Joe Owens# | 21 | 2026-2028 | |
| 45 | Wikelman Ramirez | 21 | 2024-2026 | |
| 45 | Peyton Remy | 21 | 2021-2024 | |
| 45 | Cortez Sarabia# | 21 | 2026-2028 | |
| 45 | Osiris Sierra# | 21 | 2022-2029 | |
| 45 | Nathan Webb | 21 | 2024-2025 | |
| 45 | Daiveyon Whittle# | 21 | 2022-2023 | |
| 59 | Troy Bacon | 20 | 2018-2024 | |
| 59 | Jonathan Goade# | 20 | 2026-2027 | |
| 59 | Josh MacIntosh# | 20 | 2026-2029 | |
| 59 | Luis Martinez | 20 | 2015-2017 | |
| 59 | Darren Morrison# | 20 | 2027-2029 | |
| 59 | Ofelky Peralta# | 20 | 2016-2022 | |
| 59 | Bobby Roberts | 20 | 2022-2024 | |
| 59 | Chase Smith# | 20 | 2026-2028 | |
| 59 | Christian Sosa# | 20 | 2024-2029 | |
| 59 | Evan Steele | 20 | 2019-2024 | |
| 59 | Anthony Veneziano | 20 | 2021-2025 | |
| 70 | Mike Foltynewicz | 19 | 2011-2012 | |
| 70 | Adam Laskey | 19 | 2021-2023 | |
| 70 | Ramon Lugo# | 19 | 2027-2029 | |
| 70 | Jake Odorizzi | 19 | 2024-2025 | |
| 70 | Aaron Perry | 19 | 2021-2026 | |
| 75 | Jose Alvarez | 18 | 2008-2010 | |
| 75 | Jose Bolivar# | 18 | 2022-2024 | |
| 75 | Josh Burgmann | 18 | 2021-2024 | |
| 75 | Brendan Burrows | 18 | 2022-2026 | |
| 75 | Ignacio Feliz# | 18 | 2021-2023 | |
| 75 | Adam Lukas | 18 | 2021-2023 | |
| 75 | Oddanier Mosqueda | 18 | 2019-2024 | |
| 75 | Chris Nelson# | 18 | 2029-2029 | |
| 75 | Shaun Olson# | 18 | 2027-2029 | |
| 75 | Alex Segal# | 18 | 2025-2029 | |
| 75 | Mauricio Veliz# | 18 | 2024-2028 | |
| 75 | Nick Vespi | 18 | 2017-2022 | |
| 75 | Mike Wright | 18 | 2025-2026 | |
| 88 | Clayton Andrews | 17 | 1997-1998 | |
| 88 | Blaine Boyer | 17 | 2002-2003 | |
| 88 | Chris Causey# | 17 | 2028-2029 | |
| 88 | Dylan Coleman | 17 | 2022-2025 | |
| 88 | Manny Contreras# | 17 | 2027-2028 | |
| 88 | Ken Crist# | 17 | 2026-2029 | |
| 88 | Jhonathan Diaz# | 17 | 2017-2018 | |
| 88 | Bob Dronet# | 17 | 2027-2029 | |
| 88 | Angel Gomez# | 17 | 2025-2028 | |
| 88 | Diepolt Imhoff# | 17 | 2028-2029 | |
| 88 | Dylan MacLean# | 17 | 2025-2027 | |
| 88 | Joey Matulovich | 17 | 2021-2024 | |
| 88 | Alan Rangel | 17 | 2017-2019 |
