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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Vincent Sturm# | 64 | 2051-2059 | |
| 2 | Francisco Encarnación# | 60 | 2051-2059 | |
| 3 | Rafael González | 58 | 2033-2039 | |
| 4 | Lorenzo Castillo# | 51 | 2053-2059 | |
| 4 | Raúl Pérez | 51 | 2015-2028 | |
| 6 | Fernando Reyna | 46 | 2015-2027 | |
| 7 | Ricardo Fraga | 45 | 2030-2037 | |
| 8 | Raimo Kangas | 44 | 2030-2038 | |
| 9 | Gerard Fyson | 43 | 2040-2045 | |
| 9 | Miguel Mora | 43 | 2015-2020 | |
| 11 | Sidney Jones# | 41 | 2054-2058 | |
| 11 | Joaquín Pérez | 41 | 2033-2037 | |
| 11 | José Santiago | 41 | 2028-2032 | |
| 14 | Sergio Gallegos | 39 | 2037-2041 | |
| 15 | Mark Brunswick | 38 | 2042-2048 | |
| 15 | Nick Johnston# | 38 | 2052-2058 | |
| 15 | Joe Thomas# | 38 | 2054-2058 | |
| 18 | Teddy Barnes | 37 | 2049-2052 | |
| 18 | Zion DeBose | 37 | 2030-2036 | |
| 18 | Steve Tedder | 37 | 2030-2034 | |
| 21 | Romano Martínez | 36 | 2024-2029 | |
| 21 | Horace McKenzie | 36 | 2016-2021 | |
| 21 | Dylan Telford | 36 | 2032-2036 | |
| 24 | Peyton Keys | 35 | 2043-2048 | |
| 24 | Zane Reed | 35 | 2017-2028 | |
| 24 | Scott Richardson | 35 | 2039-2045 | |
| 27 | Jeff Cook | 34 | 2051-2058 | |
| 27 | Martín Galindo | 34 | 2043-2046 | |
| 27 | Il-gyung Kim | 34 | 2017-2026 | |
| 27 | Esteban Miroz | 34 | 2027-2034 | |
| 27 | Tomiji Saikawa | 34 | 2023-2028 | |
| 32 | Ralph Owens | 33 | 2037-2043 | |
| 33 | Greg King | 32 | 2041-2045 | |
| 33 | Richie Lems# | 32 | 2051-2057 | |
| 35 | Wyatt Butler# | 31 | 2050-2054 | |
| 35 | Millard Clement# | 31 | 2051-2055 | |
| 35 | Wynn Kelley | 31 | 2042-2047 | |
| 35 | Currito Melena | 31 | 2025-2030 | |
| 35 | Adrik Mihalushkin | 31 | 2037-2041 | |
| 35 | Javier Penela | 31 | 2015-2020 | |
| 41 | Kevin Gabriel | 30 | 2042-2046 | |
| 41 | Miguel González | 30 | 2015-2018 | |
| 41 | Chih Hoong# | 30 | 2053-2056 | |
| 41 | Fernando López# | 30 | 2057-2061 | |
| 41 | Steve Ward | 30 | 2049-2052 | |
| 41 | Kent Woods | 30 | 2045-2050 | |
| 47 | Luis Castrejón | 29 | 2019-2031 | |
| 47 | Joe Gregg | 29 | 2044-2048 | |
| 47 | Xavier Padilla | 29 | 2025-2031 | |
| 50 | Carlos Díaz | 28 | 2022-2028 | |
| 50 | Floyd Emery | 28 | 2044-2048 | |
| 50 | Dawson Randolph | 28 | 2040-2044 | |
| 50 | Brieuc Robert | 28 | 2056-2059 | |
| 50 | Shan-tang Yang | 28 | 2042-2048 | |
| 50 | José Zamora# | 28 | 2051-2055 | |
| 56 | Bob Archer | 27 | 2047-2053 | |
| 56 | Sixto Espinosa# | 27 | 2053-2058 | |
| 56 | Naveed Firdausi | 27 | 2052-2057 | |
| 56 | Jack Forrest | 27 | 2045-2048 | |
| 56 | Víctor García | 27 | 2017-2021 | |
| 56 | David Jordan# | 27 | 2055-2061 | |
| 56 | Kyung-nam Kim | 27 | 2030-2034 | |
| 56 | Abakada Mana | 27 | 2033-2038 | |
| 56 | Darren Minich | 27 | 2030-2036 | |
| 56 | Juan Núñez | 27 | 2015-2018 | |
| 56 | Satoshi Ono | 27 | 2030-2035 | |
| 56 | Shawn Walker# | 27 | 2049-2053 | |
| 56 | Neil Young | 27 | 2036-2042 | |
| 69 | Fraser Chambers | 26 | 2050-2053 | |
| 69 | John Combs | 26 | 2038-2042 | |
| 69 | Héctor García | 26 | 2051-2054 | |
| 69 | Jeff Moore | 26 | 2015-2017 | |
| 69 | Bartolo Márquez | 26 | 2046-2051 | |
| 69 | Bob Payne | 26 | 2025-2027 | |
| 69 | Plinio Pedrulho | 26 | 2020-2030 | |
| 69 | Haden Pittman | 26 | 2023-2026 | |
| 69 | José Rodríguez | 26 | 2036-2041 | |
| 69 | Ricardo Sandoval# | 26 | 2053-2057 | |
| 69 | Jorge Velázquez | 26 | 2017-2025 | |
| 80 | Jules Goux | 25 | 2027-2037 | |
| 80 | Victor Lustig | 25 | 2029-2036 | |
| 80 | Jeff Merritt | 25 | 2030-2035 | |
| 80 | António Morterero | 25 | 2038-2045 | |
| 80 | Jeremy Petty | 25 | 2018-2023 | |
| 80 | Félix Torres | 25 | 2021-2026 | |
| 80 | Jeff Vázquez# | 25 | 2049-2053 | |
| 87 | Lawrence Bignold | 24 | 2016-2018 | |
| 87 | John Buck | 24 | 2015-2018 | |
| 87 | Phil Day | 24 | 2041-2043 | |
| 87 | Rio Dring | 24 | 2037-2044 | |
| 87 | Júlio Hernández | 24 | 2015-2019 | |
| 87 | Jin-soo Jan-Hui | 24 | 2037-2040 | |
| 87 | Sylvain Maire | 24 | 2052-2055 | |
| 87 | Xavier Navarro | 24 | 2023-2026 | |
| 87 | Raúl Reyes | 24 | 2041-2045 | |
| 87 | James Scott | 24 | 2018-2029 | |
| 87 | Steve Stevens# | 24 | 2055-2058 | |
| 87 | Ipe Talboom | 24 | 2024-2028 | |
| 87 | Edison Washington | 24 | 2048-2054 | |
| 100 | Tony Alfonso* | 23 | 2029-2030 |
