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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 | Raúl Pérez | 51 | 2015-2028 | |
| 3 | Fernando Reyna | 46 | 2015-2027 | |
| 4 | Ricardo Fraga# | 45 | 2030-2037 | |
| 5 | Raimo Kangas | 44 | 2030-2038 | |
| 6 | Miguel Mora | 43 | 2015-2020 | |
| 7 | Joaquín Pérez# | 41 | 2033-2037 | |
| 7 | José Santiago | 41 | 2028-2032 | |
| 9 | Sergio Gallegos | 39 | 2037-2041 | |
| 10 | Zion DeBose | 37 | 2030-2036 | |
| 10 | Steve Tedder | 37 | 2030-2034 | |
| 12 | Romano Martínez | 36 | 2024-2029 | |
| 12 | Horace McKenzie | 36 | 2016-2021 | |
| 12 | Dylan Telford | 36 | 2032-2036 | |
| 15 | Zane Reed | 35 | 2017-2028 | |
| 16 | Il-gyung Kim | 34 | 2017-2026 | |
| 16 | Esteban Miroz | 34 | 2027-2034 | |
| 16 | Tomiji Saikawa | 34 | 2023-2028 | |
| 19 | Ralph Owens# | 33 | 2037-2043 | |
| 20 | Currito Melena | 31 | 2025-2030 | |
| 20 | Adrik Mihalushkin# | 31 | 2037-2041 | |
| 20 | Javier Penela | 31 | 2015-2020 | |
| 23 | Miguel González | 30 | 2015-2018 | |
| 24 | Luis Castrejón | 29 | 2019-2031 | |
| 24 | Gerard Fyson# | 29 | 2040-2043 | |
| 24 | Xavier Padilla | 29 | 2025-2031 | |
| 27 | Carlos Díaz | 28 | 2022-2028 | |
| 27 | Dawson Randolph# | 28 | 2040-2043 | |
| 27 | Scott Richardson# | 28 | 2039-2043 | |
| 30 | Víctor García | 27 | 2017-2021 | |
| 30 | Kyung-nam Kim | 27 | 2030-2034 | |
| 30 | Abakada Mana | 27 | 2033-2038 | |
| 30 | Darren Minich | 27 | 2030-2036 | |
| 30 | Juan Núñez | 27 | 2015-2018 | |
| 30 | Satoshi Ono | 27 | 2030-2035 | |
| 30 | Neil Young# | 27 | 2036-2042 | |
| 37 | John Combs# | 26 | 2038-2042 | |
| 37 | Jeff Moore | 26 | 2015-2017 | |
| 37 | Bob Payne | 26 | 2025-2027 | |
| 37 | Plinio Pedrulho | 26 | 2020-2030 | |
| 37 | Haden Pittman | 26 | 2023-2026 | |
| 37 | José Rodríguez# | 26 | 2036-2041 | |
| 37 | Jorge Velázquez | 26 | 2017-2025 | |
| 44 | Jules Goux | 25 | 2027-2037 | |
| 44 | Victor Lustig | 25 | 2029-2036 | |
| 44 | Jeff Merritt# | 25 | 2030-2035 | |
| 44 | Jeremy Petty | 25 | 2018-2023 | |
| 44 | Félix Torres | 25 | 2021-2026 | |
| 49 | Lawrence Bignold | 24 | 2016-2018 | |
| 49 | John Buck | 24 | 2015-2018 | |
| 49 | Phil Day | 24 | 2041-2043 | |
| 49 | Júlio Hernández | 24 | 2015-2019 | |
| 49 | Jin-soo Jan-Hui# | 24 | 2037-2040 | |
| 49 | Xavier Navarro | 24 | 2023-2026 | |
| 49 | James Scott | 24 | 2018-2029 | |
| 49 | Ipe Talboom | 24 | 2024-2028 | |
| 57 | Tony Alfonso# | 23 | 2029-2030 | |
| 57 | Ryan Bentley | 23 | 2022-2024 | |
| 57 | Giuseppe Farina | 23 | 2033-2037 | |
| 57 | Alejandro García | 23 | 2032-2034 | |
| 57 | Ryan Ingram | 23 | 2023-2027 | |
| 57 | Mario López | 23 | 2029-2036 | |
| 57 | António Morterero# | 23 | 2038-2043 | |
| 57 | Matt O'Keevan | 23 | 2033-2035 | |
| 57 | Gustavo Pérez | 23 | 2018-2024 | |
| 66 | Alfonso Álvarez | 22 | 2018-2022 | |
| 66 | John Fowler | 22 | 2017-2019 | |
| 66 | César González# | 22 | 2038-2042 | |
| 66 | Daryl Keirl | 22 | 2037-2039 | |
| 66 | Sam MacKerras | 22 | 2017-2022 | |
| 66 | John Núñes# | 22 | 2035-2037 | |
| 66 | Luis Oropeza | 22 | 2030-2037 | |
| 66 | Pat Pérez | 22 | 2020-2022 | |
| 66 | John Tanner | 22 | 2015-2019 | |
| 66 | Wilson Valenzuela | 22 | 2037-2040 | |
| 76 | Larry Branch | 21 | 2015-2023 | |
| 76 | Jorge Cruz | 21 | 2025-2032 | |
| 76 | Luis Domínguez | 21 | 2026-2033 | |
| 76 | Jeff Enamorado | 21 | 2031-2034 | |
| 76 | Elroy Gardner | 21 | 2015-2019 | |
| 76 | Ricky Jackson | 21 | 2019-2024 | |
| 76 | Morgan MacDonald | 21 | 2017-2022 | |
| 76 | Kyle MacRae | 21 | 2025-2031 | |
| 76 | Leif Mayer | 21 | 2026-2028 | |
| 76 | Felipe Nieves | 21 | 2039-2042 | |
| 76 | Ainanani Oliwa# | 21 | 2033-2036 | |
| 76 | Fernando Peralta | 21 | 2017-2019 | |
| 76 | Albert Pérez | 21 | 2033-2037 | |
| 76 | Manny Pinto# | 21 | 2038-2042 | |
| 76 | Robert Smith# | 21 | 2037-2039 | |
| 76 | Noah Walker# | 21 | 2039-2041 | |
| 92 | António Aguilar | 20 | 2015-2018 | |
| 92 | Dennis Blanchard | 20 | 2033-2037 | |
| 92 | Pat Brown | 20 | 2018-2020 | |
| 92 | Carlos Cardoso | 20 | 2033-2039 | |
| 92 | Tony Cherena | 20 | 2015-2016 | |
| 92 | Walt Crouch | 20 | 2034-2036 | |
| 92 | Martyn Drdio | 20 | 2030-2037 | |
| 92 | Fernando Durán | 20 | 2023-2026 | |
| 92 | Mario Fuentes# | 20 | 2039-2042 |
