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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 | Felipe Hernández# | 45 | 2047-2053 | |
| 3 | Juan Gonzáles | 39 | 2042-2048 | |
| 3 | Salvador López | 39 | 2029-2034 | |
| 3 | Manuel Medranda | 39 | 2034-2039 | |
| 6 | Mike Barrett | 37 | 2022-2027 | |
| 6 | Woo-suk Cho | 37 | 2026-2032 | |
| 6 | Pedro Rodríguez | 37 | 2042-2048 | |
| 9 | Nicolaas de Jongh | 36 | 2031-2036 | |
| 10 | Otton Asmus | 35 | 2044-2049 | |
| 10 | José Cabrera | 35 | 2025-2028 | |
| 12 | César Morales | 34 | 2035-2038 | |
| 13 | Jesús López | 33 | 2016-2023 | |
| 13 | Bob McGhee | 33 | 2015-2028 | |
| 13 | Allen Simon | 33 | 2047-2051 | |
| 13 | Pieter Spitsbaard | 33 | 2029-2036 | |
| 13 | John Wallbank | 33 | 2030-2036 | |
| 18 | R.J. Anderson | 31 | 2020-2027 | |
| 18 | Héctor Barrera | 31 | 2038-2041 | |
| 18 | Stefan Famintsyn | 31 | 2033-2036 | |
| 21 | Shawn Arnold | 30 | 2015-2022 | |
| 21 | William Bonner | 30 | 2020-2027 | |
| 21 | Louis McDowell | 30 | 2015-2030 | |
| 21 | Scott Mildren | 30 | 2024-2027 | |
| 21 | Cisco Ortíz | 30 | 2025-2030 | |
| 21 | Júlio Palácios | 30 | 2021-2026 | |
| 21 | Zi-cheng Pei | 30 | 2039-2041 | |
| 21 | Roberto Roque | 30 | 2030-2034 | |
| 29 | António Fernández | 29 | 2033-2038 | |
| 29 | Josh Gardner | 29 | 2017-2021 | |
| 29 | Júlio Vázquez | 29 | 2027-2032 | |
| 32 | Paul Addison | 28 | 2027-2031 | |
| 32 | Clay Clark | 28 | 2015-2018 | |
| 32 | Min-chin Kim | 28 | 2030-2035 | |
| 32 | Jerry Williams | 28 | 2041-2045 | |
| 36 | Dave Farris | 27 | 2045-2048 | |
| 36 | Chris Hughes | 27 | 2033-2037 | |
| 36 | Brent Riley | 27 | 2015-2025 | |
| 39 | Travis Carson | 26 | 2020-2021 | |
| 39 | Vincent Hansen | 26 | 2045-2050 | |
| 39 | Daryl Keirl | 26 | 2031-2035 | |
| 39 | Beau Kelley# | 26 | 2048-2051 | |
| 39 | Cisco Romero | 26 | 2019-2022 | |
| 39 | Pedro Romero | 26 | 2020-2026 | |
| 39 | Cristóbal Román | 26 | 2036-2038 | |
| 39 | Rob Smith | 26 | 2018-2027 | |
| 47 | Jesús Bruno | 25 | 2038-2042 | |
| 47 | Jorge Carrión | 25 | 2022-2026 | |
| 47 | Victor de Meij | 25 | 2025-2032 | |
| 47 | Jeff Moore | 25 | 2020-2022 | |
| 47 | Santiago Ramírez | 25 | 2030-2034 | |
| 47 | Javier Roldán | 25 | 2019-2023 | |
| 47 | César Soto | 25 | 2033-2035 | |
| 47 | Sixto Soto | 25 | 2028-2034 | |
| 47 | Mark Tucker | 25 | 2017-2021 | |
| 47 | Tom Young | 25 | 2044-2050 | |
| 57 | Greg Borges | 24 | 2038-2042 | |
| 57 | Cipriano Bustamante | 24 | 2042-2045 | |
| 57 | Jerry Cherry | 24 | 2039-2043 | |
| 57 | César González | 24 | 2021-2023 | |
| 57 | Tom Hancock# | 24 | 2050-2054 | |
| 57 | Chris Hayes | 24 | 2023-2027 | |
| 57 | Maximiano Mealha | 24 | 2033-2037 | |
| 57 | Seong-hyeon Pak | 24 | 2031-2035 | |
| 57 | Eric Patnode | 24 | 2016-2025 | |
| 57 | Brian Patterson | 24 | 2040-2045 | |
| 57 | Jackson Williams | 24 | 2034-2040 | |
| 68 | Jason Ackerman | 23 | 2015-2022 | |
| 68 | Álex Carrillo | 23 | 2018-2021 | |
| 68 | Alfredo Casas | 23 | 2047-2052 | |
| 68 | António Fabián | 23 | 2020-2028 | |
| 68 | Ralph Haggerty | 23 | 2027-2030 | |
| 68 | Sam Johnston | 23 | 2037-2039 | |
| 68 | Delmar Llerena | 23 | 2026-2032 | |
| 68 | Jorge Moreno | 23 | 2036-2039 | |
| 68 | Patrick Nicolas | 23 | 2034-2039 | |
| 68 | Homer O'Lannigan | 23 | 2018-2021 | |
| 68 | Juan Ramírez# | 23 | 2050-2053 | |
| 68 | Hartmann Riedman | 23 | 2024-2027 | |
| 68 | Alex Simmons | 23 | 2017-2024 | |
| 68 | Tim Simmons | 23 | 2047-2051 | |
| 68 | Dionísio Zagallo# | 23 | 2051-2052 | |
| 83 | Eurauraga Attunga | 22 | 2034-2038 | |
| 83 | Chris Burgess | 22 | 2022-2027 | |
| 83 | Atila Freska | 22 | 2026-2028 | |
| 83 | Myles Jones# | 22 | 2049-2053 | |
| 83 | Gerald Keller | 22 | 2026-2029 | |
| 83 | Miguel López | 22 | 2026-2028 | |
| 83 | Katsumoto Miyanohara | 22 | 2029-2033 | |
| 83 | Vicente Molina# | 22 | 2040-2044 | |
| 83 | Ethan Morse# | 22 | 2048-2052 | |
| 83 | Homer Shafer | 22 | 2015-2020 | |
| 83 | Ray Thibaut | 22 | 2015-2019 | |
| 83 | Orlando Uribe | 22 | 2025-2031 | |
| 83 | José Vargo | 22 | 2022-2024 | |
| 83 | Steven Williams | 22 | 2015-2019 | |
| 83 | Yoriyoshi Yoshimura | 22 | 2028-2030 | |
| 98 | Mick Alston | 21 | 2028-2036 | |
| 98 | Loren Berdine | 21 | 2032-2034 | |
| 98 | José Blanco | 21 | 2032-2034 |
