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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Rafael González | 58 | 2033-2039 | |
| 2 | Francisco Encarnación# | 53 | 2051-2057 | |
| 3 | Raúl Pérez | 51 | 2015-2028 | |
| 4 | Fernando Reyna | 46 | 2015-2027 | |
| 5 | Ricardo Fraga | 45 | 2030-2037 | |
| 5 | Vincent Sturm# | 45 | 2051-2057 | |
| 7 | Raimo Kangas | 44 | 2030-2038 | |
| 8 | Gerard Fyson | 43 | 2040-2045 | |
| 8 | Miguel Mora | 43 | 2015-2020 | |
| 10 | Joaquín Pérez | 41 | 2033-2037 | |
| 10 | José Santiago | 41 | 2028-2032 | |
| 12 | Sergio Gallegos | 39 | 2037-2041 | |
| 13 | Mark Brunswick | 38 | 2042-2048 | |
| 14 | Teddy Barnes | 37 | 2049-2052 | |
| 14 | Zion DeBose | 37 | 2030-2036 | |
| 14 | Nick Johnston# | 37 | 2052-2057 | |
| 14 | Steve Tedder | 37 | 2030-2034 | |
| 18 | Romano Martínez | 36 | 2024-2029 | |
| 18 | Horace McKenzie | 36 | 2016-2021 | |
| 18 | Dylan Telford | 36 | 2032-2036 | |
| 21 | Peyton Keys | 35 | 2043-2048 | |
| 21 | Zane Reed | 35 | 2017-2028 | |
| 21 | Scott Richardson | 35 | 2039-2045 | |
| 24 | Martín Galindo | 34 | 2043-2046 | |
| 24 | Il-gyung Kim | 34 | 2017-2026 | |
| 24 | Esteban Miroz | 34 | 2027-2034 | |
| 24 | Tomiji Saikawa | 34 | 2023-2028 | |
| 28 | Lorenzo Castillo# | 33 | 2053-2057 | |
| 28 | Ralph Owens | 33 | 2037-2043 | |
| 30 | Greg King | 32 | 2041-2045 | |
| 30 | Richie Lems# | 32 | 2051-2057 | |
| 32 | Wyatt Butler# | 31 | 2050-2054 | |
| 32 | Millard Clement# | 31 | 2051-2055 | |
| 32 | Jeff Cook# | 31 | 2051-2057 | |
| 32 | Wynn Kelley | 31 | 2042-2047 | |
| 32 | Currito Melena | 31 | 2025-2030 | |
| 32 | Adrik Mihalushkin | 31 | 2037-2041 | |
| 32 | Javier Penela | 31 | 2015-2020 | |
| 39 | Kevin Gabriel | 30 | 2042-2046 | |
| 39 | Miguel González | 30 | 2015-2018 | |
| 39 | Chih Hoong# | 30 | 2053-2056 | |
| 39 | Sidney Jones# | 30 | 2054-2057 | |
| 39 | Steve Ward# | 30 | 2049-2052 | |
| 39 | Kent Woods | 30 | 2045-2050 | |
| 45 | Luis Castrejón | 29 | 2019-2031 | |
| 45 | Joe Gregg | 29 | 2044-2048 | |
| 45 | Xavier Padilla | 29 | 2025-2031 | |
| 48 | Carlos Díaz | 28 | 2022-2028 | |
| 48 | Floyd Emery | 28 | 2044-2048 | |
| 48 | Dawson Randolph | 28 | 2040-2044 | |
| 48 | Joe Thomas# | 28 | 2054-2057 | |
| 48 | Shan-tang Yang | 28 | 2042-2048 | |
| 48 | José Zamora# | 28 | 2051-2055 | |
| 54 | Bob Archer | 27 | 2047-2053 | |
| 54 | Naveed Firdausi# | 27 | 2052-2057 | |
| 54 | Jack Forrest | 27 | 2045-2048 | |
| 54 | Víctor García | 27 | 2017-2021 | |
| 54 | Kyung-nam Kim | 27 | 2030-2034 | |
| 54 | Abakada Mana | 27 | 2033-2038 | |
| 54 | Darren Minich | 27 | 2030-2036 | |
| 54 | Juan Núñez | 27 | 2015-2018 | |
| 54 | Satoshi Ono | 27 | 2030-2035 | |
| 54 | Shawn Walker# | 27 | 2049-2053 | |
| 54 | Neil Young | 27 | 2036-2042 | |
| 65 | Fraser Chambers# | 26 | 2050-2053 | |
| 65 | John Combs | 26 | 2038-2042 | |
| 65 | Héctor García | 26 | 2051-2054 | |
| 65 | Jeff Moore | 26 | 2015-2017 | |
| 65 | Bartolo Márquez | 26 | 2046-2051 | |
| 65 | Bob Payne | 26 | 2025-2027 | |
| 65 | Plinio Pedrulho | 26 | 2020-2030 | |
| 65 | Haden Pittman | 26 | 2023-2026 | |
| 65 | José Rodríguez | 26 | 2036-2041 | |
| 65 | Ricardo Sandoval# | 26 | 2053-2057 | |
| 65 | Jorge Velázquez | 26 | 2017-2025 | |
| 76 | Jules Goux | 25 | 2027-2037 | |
| 76 | Victor Lustig | 25 | 2029-2036 | |
| 76 | Jeff Merritt | 25 | 2030-2035 | |
| 76 | António Morterero | 25 | 2038-2045 | |
| 76 | Jeremy Petty | 25 | 2018-2023 | |
| 76 | Félix Torres | 25 | 2021-2026 | |
| 76 | Jeff Vázquez# | 25 | 2049-2053 | |
| 83 | Lawrence Bignold | 24 | 2016-2018 | |
| 83 | John Buck | 24 | 2015-2018 | |
| 83 | Phil Day | 24 | 2041-2043 | |
| 83 | Rio Dring | 24 | 2037-2044 | |
| 83 | Júlio Hernández | 24 | 2015-2019 | |
| 83 | Jin-soo Jan-Hui | 24 | 2037-2040 | |
| 83 | Sylvain Maire# | 24 | 2052-2055 | |
| 83 | Xavier Navarro | 24 | 2023-2026 | |
| 83 | Raúl Reyes | 24 | 2041-2045 | |
| 83 | James Scott | 24 | 2018-2029 | |
| 83 | Ipe Talboom | 24 | 2024-2028 | |
| 83 | Edison Washington | 24 | 2048-2054 | |
| 95 | Tony Alfonso* | 23 | 2029-2030 | |
| 95 | Ryan Bentley | 23 | 2022-2024 | |
| 95 | Greg Carter# | 23 | 2050-2056 | |
| 95 | Giuseppe Farina | 23 | 2033-2037 | |
| 95 | Alejandro García | 23 | 2032-2034 | |
| 95 | Luis Gutiérrez# | 23 | 2046-2052 |
