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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Juju Kirby# | 24 | 2052-2056 | |
| 2 | Ron Dykstra | 21 | 2052-2054 | |
| 3 | Johnny De La Cruz# | 20 | 2053-2055 | |
| 3 | Chase Jones | 20 | 2050-2053 | |
| 3 | Santiago Rendon | 20 | 2042-2046 | |
| 3 | Gabe Soares | 20 | 2043-2046 | |
| 3 | Paul Wormley# | 20 | 2052-2056 | |
| 8 | Levi Guajardo | 19 | 2050-2055 | |
| 8 | Aiden McKeown | 19 | 2051-2054 | |
| 8 | Pedro Tapia | 19 | 2034-2038 | |
| 8 | Doug Walston# | 19 | 2056-2059 | |
| 12 | Woody Anderson | 18 | 2050-2054 | |
| 12 | Humberto Balderrama | 18 | 2011-2014 | |
| 12 | Jose Benitez | 18 | 2028-2030 | |
| 12 | Pedro Carrillo | 18 | 2021-2025 | |
| 12 | Randy Chapin | 18 | 2053-2056 | |
| 12 | Santiago Flores | 18 | 2043-2046 | |
| 12 | Bert Leyva | 18 | 2023-2025 | |
| 12 | Bill Parra | 18 | 2019-2022 | |
| 12 | Tristan Sanders | 18 | 2029-2031 | |
| 21 | Stan Betancourt | 17 | 2036-2038 | |
| 21 | Lindsey Ceballos# | 17 | 2056-2058 | |
| 21 | Ben Claflin | 17 | 2006-2009 | |
| 21 | Mario Hagi | 17 | 2054-2057 | |
| 21 | Marcio Ramírez# | 17 | 2055-2058 | |
| 21 | Jeremy Robinson | 17 | 2028-2030 | |
| 21 | Quinto Sol | 17 | 2034-2037 | |
| 21 | Aarón Soto | 17 | 2043-2044 | |
| 21 | Tyler Tanner | 17 | 2048-2051 | |
| 30 | Kyle Baker | 16 | 2039-2040 | |
| 30 | Emmanuel Carrasco# | 16 | 2056-2058 | |
| 30 | Taylor Hendrickson# | 16 | 2054-2059 | |
| 30 | Ramón Huitron | 16 | 2039-2040 | |
| 30 | Logan McKain | 16 | 2032-2035 | |
| 30 | Angel Molina | 16 | 2015-2017 | |
| 30 | Duke Petty | 16 | 2048-2051 | |
| 30 | King Sharp | 16 | 2039-2040 | |
| 30 | Wade Trent | 16 | 2037-2038 | |
| 30 | Ryan Tyler | 16 | 2006-2009 | |
| 40 | Mason Biondo | 15 | 2047-2049 | |
| 40 | Matt Carter | 15 | 2030-2031 | |
| 40 | Montana Caulder | 15 | 2039-2040 | |
| 40 | Woody Duncan# | 15 | 2057-2059 | |
| 40 | Aaron Evans | 15 | 2028-2029 | |
| 40 | Solomon Gildner | 15 | 2031-2032 | |
| 40 | Ian Gutenberg | 15 | 2033-2034 | |
| 40 | Jeff Kesel | 15 | 2030-2032 | |
| 40 | Liberato Martínez | 15 | 2053-2056 | |
| 40 | Fadil Paterson# | 15 | 2053-2056 | |
| 40 | Quinn Ricketts | 15 | 2023-2026 | |
| 40 | Brad Rumfield | 15 | 2013-2015 | |
| 40 | R.J. Trent | 15 | 2046-2047 | |
| 40 | Kevin Velazquez | 15 | 2043-2045 | |
| 54 | Santiago Arredondo | 14 | 2036-2039 | |
| 54 | Joey Cossey | 14 | 2039-2040 | |
| 54 | Yoan Carlos Crespo | 14 | 2046-2047 | |
| 54 | Christian Cunningham | 14 | 2044-2046 | |
| 54 | Jude DeLeo | 14 | 2048-2052 | |
| 54 | Nestor Diaz | 14 | 2011-2013 | |
| 54 | Tarren Farnsworth | 14 | 2038-2040 | |
| 54 | Horacio Galli | 14 | 2034-2036 | |
| 54 | Javier González | 14 | 2034-2036 | |
| 54 | Fernando Guizar | 14 | 2030-2033 | |
| 54 | B.J. Hart# | 14 | 2053-2055 | |
| 54 | John Hazen | 14 | 2044-2047 | |
| 54 | Francisco Hernandez | 14 | 2011-2013 | |
| 54 | Bill Iacullo | 14 | 2018-2020 | |
| 54 | Luther Justus# | 14 | 2054-2056 | |
| 54 | Adam Lessard | 14 | 2017-2018 | |
| 54 | Malachi Levi | 14 | 2042-2043 | |
| 54 | Vitale Lupino | 14 | 2016-2018 | |
| 54 | Adrian Marchione# | 14 | 2049-2050 | |
| 54 | Mike Marquez | 14 | 2017-2019 | |
| 54 | Harrison Niemczura | 14 | 2039-2041 | |
| 54 | Ian O'Connell | 14 | 2041-2042 | |
| 54 | Danny Pankratz | 14 | 2028-2029 | |
| 54 | John Phillips# | 14 | 2054-2055 | |
| 54 | Dario Rios | 14 | 2028-2029 | |
| 54 | Cortez Rioz | 14 | 2034-2036 | |
| 54 | Alejandro Santana | 14 | 2039-2040 | |
| 54 | Sparky Stapleton | 14 | 2048-2050 | |
| 54 | Jayce Stark | 14 | 2051-2053 | |
| 54 | Jason Stephan | 14 | 2021-2024 | |
| 54 | Ian Tripp# | 14 | 2053-2055 | |
| 54 | Amauris Ureña | 14 | 2046-2047 | |
| 54 | Kevin Villeda | 14 | 2034-2037 | |
| 87 | Jayden Adcock# | 13 | 2057-2059 | |
| 87 | Jools Anthony# | 13 | 2051-2052 | |
| 87 | Miguel Arriola | 13 | 2046-2047 | |
| 87 | Jorge Bahena | 13 | 2020-2021 | |
| 87 | Daniel Berndt | 13 | 2025-2028 | |
| 87 | Austin Birmingham | 13 | 2049-2052 | |
| 87 | Joseph Boonsook# | 13 | 2051-2052 | |
| 87 | Isaac Brock# | 13 | 2054-2056 | |
| 87 | Neymar Castaneda# | 13 | 2053-2055 | |
| 87 | Ismael Centeno | 13 | 2028-2030 | |
| 87 | Steve Clark# | 13 | 2045-2047 | |
| 87 | Justin Doherty | 13 | 2022-2024 | |
| 87 | Jordan Esini | 13 | 2019-2022 | |
| 87 | Martin García | 13 | 2032-2035 |
