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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | David Davis | 46 | 2019-2030 | |
| 2 | Salvador López | 39 | 2029-2034 | |
| 2 | Manuel Medranda | 39 | 2034-2039 | |
| 4 | Mike Barrett | 37 | 2022-2027 | |
| 4 | Woo-suk Cho | 37 | 2026-2032 | |
| 6 | Nicolaas de Jongh | 36 | 2031-2036 | |
| 7 | José Cabrera | 35 | 2025-2028 | |
| 8 | César Morales | 34 | 2035-2038 | |
| 9 | Jesús López | 33 | 2016-2023 | |
| 9 | Bob McGhee | 33 | 2015-2028 | |
| 9 | Pieter Spitsbaard | 33 | 2029-2036 | |
| 9 | John Wallbank | 33 | 2030-2036 | |
| 13 | R.J. Anderson | 31 | 2020-2027 | |
| 13 | Héctor Barrera# | 31 | 2038-2041 | |
| 13 | Stefan Famintsyn | 31 | 2033-2036 | |
| 16 | Shawn Arnold | 30 | 2015-2022 | |
| 16 | William Bonner | 30 | 2020-2027 | |
| 16 | Louis McDowell | 30 | 2015-2030 | |
| 16 | Scott Mildren | 30 | 2024-2027 | |
| 16 | Cisco Ortíz | 30 | 2025-2030 | |
| 16 | Júlio Palácios | 30 | 2021-2026 | |
| 16 | Zi-cheng Pei# | 30 | 2039-2041 | |
| 16 | Roberto Roque | 30 | 2030-2034 | |
| 24 | António Fernández | 29 | 2033-2038 | |
| 24 | Josh Gardner | 29 | 2017-2021 | |
| 24 | Pedro Rodríguez# | 29 | 2042-2045 | |
| 24 | Júlio Vázquez | 29 | 2027-2032 | |
| 28 | Paul Addison | 28 | 2027-2031 | |
| 28 | Clay Clark | 28 | 2015-2018 | |
| 28 | Min-chin Kim | 28 | 2030-2035 | |
| 28 | Jerry Williams# | 28 | 2041-2045 | |
| 32 | Chris Hughes | 27 | 2033-2037 | |
| 32 | Brent Riley | 27 | 2015-2025 | |
| 34 | Travis Carson | 26 | 2020-2021 | |
| 34 | Daryl Keirl | 26 | 2031-2035 | |
| 34 | Cisco Romero | 26 | 2019-2022 | |
| 34 | Pedro Romero | 26 | 2020-2026 | |
| 34 | Cristóbal Román | 26 | 2036-2038 | |
| 34 | Rob Smith | 26 | 2018-2027 | |
| 40 | Jesús Bruno | 25 | 2038-2042 | |
| 40 | Jorge Carrión | 25 | 2022-2026 | |
| 40 | Victor de Meij | 25 | 2025-2032 | |
| 40 | Jeff Moore | 25 | 2020-2022 | |
| 40 | Santiago Ramírez | 25 | 2030-2034 | |
| 40 | Javier Roldán | 25 | 2019-2023 | |
| 40 | César Soto | 25 | 2033-2035 | |
| 40 | Sixto Soto | 25 | 2028-2034 | |
| 40 | Mark Tucker | 25 | 2017-2021 | |
| 49 | Greg Borges | 24 | 2038-2042 | |
| 49 | Cipriano Bustamante# | 24 | 2042-2045 | |
| 49 | Jerry Cherry# | 24 | 2039-2043 | |
| 49 | César González | 24 | 2021-2023 | |
| 49 | Chris Hayes | 24 | 2023-2027 | |
| 49 | Maximiano Mealha | 24 | 2033-2037 | |
| 49 | Seong-hyeon Pak | 24 | 2031-2035 | |
| 49 | Eric Patnode | 24 | 2016-2025 | |
| 49 | Brian Patterson# | 24 | 2040-2045 | |
| 49 | Jackson Williams | 24 | 2034-2040 | |
| 59 | Jason Ackerman | 23 | 2015-2022 | |
| 59 | Álex Carrillo | 23 | 2018-2021 | |
| 59 | António Fabián | 23 | 2020-2028 | |
| 59 | Ralph Haggerty | 23 | 2027-2030 | |
| 59 | Sam Johnston | 23 | 2037-2039 | |
| 59 | Delmar Llerena | 23 | 2026-2032 | |
| 59 | Jorge Moreno | 23 | 2036-2039 | |
| 59 | Patrick Nicolas | 23 | 2034-2039 | |
| 59 | Homer O'Lannigan | 23 | 2018-2021 | |
| 59 | Hartmann Riedman | 23 | 2024-2027 | |
| 59 | Alex Simmons | 23 | 2017-2024 | |
| 70 | Eurauraga Attunga | 22 | 2034-2038 | |
| 70 | Chris Burgess | 22 | 2022-2027 | |
| 70 | Atila Freska | 22 | 2026-2028 | |
| 70 | Gerald Keller | 22 | 2026-2029 | |
| 70 | Miguel López | 22 | 2026-2028 | |
| 70 | Katsumoto Miyanohara | 22 | 2029-2033 | |
| 70 | Vicente Molina# | 22 | 2040-2044 | |
| 70 | Homer Shafer | 22 | 2015-2020 | |
| 70 | Ray Thibaut | 22 | 2015-2019 | |
| 70 | Orlando Uribe | 22 | 2025-2031 | |
| 70 | José Vargo | 22 | 2022-2024 | |
| 70 | Steven Williams | 22 | 2015-2019 | |
| 70 | Yoriyoshi Yoshimura | 22 | 2028-2030 | |
| 83 | Mick Alston | 21 | 2028-2036 | |
| 83 | Loren Berdine | 21 | 2032-2034 | |
| 83 | José Blanco# | 21 | 2032-2034 | |
| 83 | Virgil Dickerson# | 21 | 2040-2041 | |
| 83 | David Fuentes | 21 | 2035-2043 | |
| 83 | Elmer García | 21 | 2021-2028 | |
| 83 | Gabriel García# | 21 | 2042-2045 | |
| 83 | Herman Griffin# | 21 | 2041-2043 | |
| 83 | Dorian Gunther | 21 | 2036-2039 | |
| 83 | Peter Hall | 21 | 2024-2028 | |
| 83 | Andrew Holloway | 21 | 2028-2032 | |
| 83 | Jesús Lara | 21 | 2030-2037 | |
| 83 | Grover Lowdermilk | 21 | 2029-2033 | |
| 83 | Eric Manchester# | 21 | 2039-2041 | |
| 83 | Octávio Rodríguez | 21 | 2029-2032 | |
| 83 | Ángel Roldán | 21 | 2033-2036 | |
| 83 | Mike Russell | 21 | 2018-2022 | |
| 83 | Maxwell Simon | 21 | 2024-2027 |
