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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 | |
| 9 | Steve Green# | 36 | 2054-2058 | |
| 11 | Otton Asmus | 35 | 2044-2049 | |
| 11 | José Cabrera | 35 | 2025-2028 | |
| 13 | John Bunch | 34 | 2054-2058 | |
| 13 | César Morales | 34 | 2035-2038 | |
| 15 | Jesús López | 33 | 2016-2023 | |
| 15 | Bob McGhee | 33 | 2015-2028 | |
| 15 | Fernando Rivera# | 33 | 2054-2060 | |
| 15 | Allen Simon | 33 | 2047-2051 | |
| 15 | Pieter Spitsbaard | 33 | 2029-2036 | |
| 15 | John Wallbank | 33 | 2030-2036 | |
| 21 | Brody Avery | 32 | 2054-2057 | |
| 21 | Tom Hancock | 32 | 2050-2055 | |
| 23 | R.J. Anderson | 31 | 2020-2027 | |
| 23 | Héctor Barrera | 31 | 2038-2041 | |
| 23 | Stefan Famintsyn | 31 | 2033-2036 | |
| 23 | Rod Pritchard# | 31 | 2057-2060 | |
| 27 | Shawn Arnold | 30 | 2015-2022 | |
| 27 | William Bonner | 30 | 2020-2027 | |
| 27 | Louis McDowell | 30 | 2015-2030 | |
| 27 | Scott Mildren | 30 | 2024-2027 | |
| 27 | Cisco Ortíz | 30 | 2025-2030 | |
| 27 | Júlio Palácios | 30 | 2021-2026 | |
| 27 | Zi-cheng Pei | 30 | 2039-2041 | |
| 27 | Roberto Roque | 30 | 2030-2034 | |
| 35 | António Fernández | 29 | 2033-2038 | |
| 35 | Josh Gardner | 29 | 2017-2021 | |
| 35 | Woody Johnston# | 29 | 2056-2062 | |
| 35 | Júlio Vázquez | 29 | 2027-2032 | |
| 35 | Albert Wallace# | 29 | 2053-2056 | |
| 40 | Paul Addison | 28 | 2027-2031 | |
| 40 | Clay Clark | 28 | 2015-2018 | |
| 40 | Min-chin Kim | 28 | 2030-2035 | |
| 40 | Ken O'Neal | 28 | 2054-2057 | |
| 40 | Jerry Williams | 28 | 2041-2045 | |
| 45 | Jim Bird# | 27 | 2054-2058 | |
| 45 | James Ellison# | 27 | 2054-2056 | |
| 45 | Dave Farris | 27 | 2045-2048 | |
| 45 | Chris Hughes | 27 | 2033-2037 | |
| 45 | Brent Riley | 27 | 2015-2025 | |
| 50 | Travis Carson | 26 | 2020-2021 | |
| 50 | Tom Evans | 26 | 2054-2057 | |
| 50 | Vincent Hansen | 26 | 2045-2050 | |
| 50 | Daryl Keirl | 26 | 2031-2035 | |
| 50 | Beau Kelley | 26 | 2048-2051 | |
| 50 | Cisco Romero | 26 | 2019-2022 | |
| 50 | Pedro Romero | 26 | 2020-2026 | |
| 50 | Cristóbal Román | 26 | 2036-2038 | |
| 50 | Rob Smith | 26 | 2018-2027 | |
| 59 | Jesús Bruno | 25 | 2038-2042 | |
| 59 | Jorge Carrión | 25 | 2022-2026 | |
| 59 | Victor de Meij | 25 | 2025-2032 | |
| 59 | Jim Lee | 25 | 2057-2061 | |
| 59 | Jeff Moore | 25 | 2020-2022 | |
| 59 | Santiago Ramírez | 25 | 2030-2034 | |
| 59 | Javier Roldán | 25 | 2019-2023 | |
| 59 | César Soto | 25 | 2033-2035 | |
| 59 | Sixto Soto | 25 | 2028-2034 | |
| 59 | Mark Tucker | 25 | 2017-2021 | |
| 59 | Tom Young | 25 | 2044-2050 | |
| 70 | Greg Borges | 24 | 2038-2042 | |
| 70 | Cipriano Bustamante | 24 | 2042-2045 | |
| 70 | Jerry Cherry | 24 | 2039-2043 | |
| 70 | César González | 24 | 2021-2023 | |
| 70 | Chris Hayes | 24 | 2023-2027 | |
| 70 | Charles Lawrence | 24 | 2054-2056 | |
| 70 | Maximiano Mealha | 24 | 2033-2037 | |
| 70 | Seong-hyeon Pak | 24 | 2031-2035 | |
| 70 | Eric Patnode | 24 | 2016-2025 | |
| 70 | Brian Patterson | 24 | 2040-2045 | |
| 70 | Jackson Williams | 24 | 2034-2040 | |
| 81 | Jason Ackerman | 23 | 2015-2022 | |
| 81 | Álex Carrillo | 23 | 2018-2021 | |
| 81 | Alfredo Casas | 23 | 2047-2052 | |
| 81 | Brian Dalton | 23 | 2054-2058 | |
| 81 | Jaime Delegorsa | 23 | 2052-2057 | |
| 81 | António Fabián | 23 | 2020-2028 | |
| 81 | Ralph Haggerty | 23 | 2027-2030 | |
| 81 | Sam Johnston | 23 | 2037-2039 | |
| 81 | Gerald Jones# | 23 | 2056-2059 | |
| 81 | Delmar Llerena | 23 | 2026-2032 | |
| 81 | Jorge Moreno | 23 | 2036-2039 | |
| 81 | Patrick Nicolas | 23 | 2034-2039 | |
| 81 | Homer O'Lannigan | 23 | 2018-2021 | |
| 81 | Juan Ramírez | 23 | 2050-2053 | |
| 81 | Hartmann Riedman | 23 | 2024-2027 | |
| 81 | Alex Simmons | 23 | 2017-2024 | |
| 81 | Tim Simmons | 23 | 2047-2051 | |
| 81 | Richard Stevenson# | 23 | 2058-2062 | |
| 81 | Dionísio Zagallo# | 23 | 2051-2052 | |
| 100 | Brady Allen# | 22 | 2059-2063 |
