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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 | Gerard Fyson | 43 | 2040-2045 | |
| 6 | Miguel Mora | 43 | 2015-2020 | |
| 8 | Joaquín Pérez | 41 | 2033-2037 | |
| 8 | José Santiago | 41 | 2028-2032 | |
| 10 | Sergio Gallegos | 39 | 2037-2041 | |
| 11 | Zion DeBose | 37 | 2030-2036 | |
| 11 | Steve Tedder | 37 | 2030-2034 | |
| 13 | Romano Martínez | 36 | 2024-2029 | |
| 13 | Horace McKenzie | 36 | 2016-2021 | |
| 13 | Dylan Telford | 36 | 2032-2036 | |
| 16 | Zane Reed | 35 | 2017-2028 | |
| 16 | Scott Richardson | 35 | 2039-2045 | |
| 18 | Martín Galindo# | 34 | 2043-2046 | |
| 18 | Il-gyung Kim | 34 | 2017-2026 | |
| 18 | Esteban Miroz | 34 | 2027-2034 | |
| 18 | Tomiji Saikawa | 34 | 2023-2028 | |
| 22 | Ralph Owens | 33 | 2037-2043 | |
| 23 | Greg King# | 32 | 2041-2045 | |
| 24 | Currito Melena | 31 | 2025-2030 | |
| 24 | Adrik Mihalushkin | 31 | 2037-2041 | |
| 24 | Javier Penela | 31 | 2015-2020 | |
| 27 | Kevin Gabriel# | 30 | 2042-2046 | |
| 27 | Miguel González | 30 | 2015-2018 | |
| 29 | Luis Castrejón | 29 | 2019-2031 | |
| 29 | Wynn Kelley# | 29 | 2042-2046 | |
| 29 | Xavier Padilla | 29 | 2025-2031 | |
| 32 | Mark Brunswick# | 28 | 2042-2046 | |
| 32 | Carlos Díaz | 28 | 2022-2028 | |
| 32 | Dawson Randolph | 28 | 2040-2044 | |
| 35 | Víctor García | 27 | 2017-2021 | |
| 35 | Kyung-nam Kim | 27 | 2030-2034 | |
| 35 | Abakada Mana | 27 | 2033-2038 | |
| 35 | Darren Minich | 27 | 2030-2036 | |
| 35 | Juan Núñez | 27 | 2015-2018 | |
| 35 | Satoshi Ono | 27 | 2030-2035 | |
| 35 | Neil Young# | 27 | 2036-2042 | |
| 42 | John Combs | 26 | 2038-2042 | |
| 42 | Jeff Moore | 26 | 2015-2017 | |
| 42 | Bob Payne | 26 | 2025-2027 | |
| 42 | Plinio Pedrulho | 26 | 2020-2030 | |
| 42 | Haden Pittman | 26 | 2023-2026 | |
| 42 | José Rodríguez | 26 | 2036-2041 | |
| 42 | Jorge Velázquez | 26 | 2017-2025 | |
| 49 | Jules Goux | 25 | 2027-2037 | |
| 49 | Victor Lustig | 25 | 2029-2036 | |
| 49 | Jeff Merritt | 25 | 2030-2035 | |
| 49 | António Morterero# | 25 | 2038-2045 | |
| 49 | Jeremy Petty | 25 | 2018-2023 | |
| 49 | Félix Torres | 25 | 2021-2026 | |
| 55 | Lawrence Bignold | 24 | 2016-2018 | |
| 55 | John Buck | 24 | 2015-2018 | |
| 55 | Phil Day | 24 | 2041-2043 | |
| 55 | Rio Dring# | 24 | 2037-2044 | |
| 55 | Júlio Hernández | 24 | 2015-2019 | |
| 55 | Jin-soo Jan-Hui | 24 | 2037-2040 | |
| 55 | Xavier Navarro | 24 | 2023-2026 | |
| 55 | Raúl Reyes# | 24 | 2041-2045 | |
| 55 | James Scott | 24 | 2018-2029 | |
| 55 | Ipe Talboom | 24 | 2024-2028 | |
| 65 | Tony Alfonso# | 23 | 2029-2030 | |
| 65 | Ryan Bentley | 23 | 2022-2024 | |
| 65 | Giuseppe Farina | 23 | 2033-2037 | |
| 65 | Alejandro García | 23 | 2032-2034 | |
| 65 | Ryan Ingram | 23 | 2023-2027 | |
| 65 | Mario López | 23 | 2029-2036 | |
| 65 | Matt O'Keevan | 23 | 2033-2035 | |
| 65 | Gustavo Pérez | 23 | 2018-2024 | |
| 73 | Joop Els# | 22 | 2041-2044 | |
| 73 | Floyd Emery# | 22 | 2044-2046 | |
| 73 | John Fowler | 22 | 2017-2019 | |
| 73 | César González | 22 | 2038-2042 | |
| 73 | Daryl Keirl | 22 | 2037-2039 | |
| 73 | Sam MacKerras | 22 | 2017-2022 | |
| 73 | John Núñes | 22 | 2035-2037 | |
| 73 | Luis Oropeza | 22 | 2030-2037 | |
| 73 | Pat Pérez | 22 | 2020-2022 | |
| 73 | John Tanner | 22 | 2015-2019 | |
| 73 | Wilson Valenzuela | 22 | 2037-2040 | |
| 73 | Alfonso Álvarez | 22 | 2018-2022 | |
| 85 | Larry Branch | 21 | 2015-2023 | |
| 85 | Jorge Cruz | 21 | 2025-2032 | |
| 85 | Luis Domínguez | 21 | 2026-2033 | |
| 85 | Jeff Enamorado | 21 | 2031-2034 | |
| 85 | Elroy Gardner | 21 | 2015-2019 | |
| 85 | Ricky Jackson | 21 | 2019-2024 | |
| 85 | Morgan MacDonald | 21 | 2017-2022 | |
| 85 | Kyle MacRae | 21 | 2025-2031 | |
| 85 | Leif Mayer | 21 | 2026-2028 | |
| 85 | Felipe Nieves | 21 | 2039-2042 | |
| 85 | Ainanani Oliwa# | 21 | 2033-2036 | |
| 85 | Fernando Peralta | 21 | 2017-2019 | |
| 85 | Manny Pinto | 21 | 2038-2042 | |
| 85 | Albert Pérez | 21 | 2033-2037 | |
| 85 | Robert Smith | 21 | 2037-2039 | |
| 85 | Noah Walker# | 21 | 2039-2041 |
