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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Victor Brey | 72 | 2021-2028 | |
| 2 | Marvin Stevens | 55 | 2043-2056 | |
| 3 | Willie Cameron | 54 | 2016-2031 | |
| 4 | Vic Lee | 49 | 2049-2058 | |
| 5 | Noboru Kokawa# | 48 | 2048-2054 | |
| 6 | Ikaia Duncalf | 47 | 2045-2054 | |
| 7 | Patrick Ibáñez | 46 | 2035-2046 | |
| 7 | Pedro Negrón | 46 | 2050-2058 | |
| 9 | Matt Davenport | 45 | 2029-2037 | |
| 9 | António López | 45 | 2041-2050 | |
| 11 | Edmund Rochefort | 44 | 2050-2057 | |
| 12 | Danny Byrd | 43 | 2044-2050 | |
| 12 | Robert Carlson | 43 | 2053-2057 | |
| 12 | Luis Hernández | 43 | 2030-2037 | |
| 12 | Cisco Pérez | 43 | 2034-2038 | |
| 16 | Mario Silva | 42 | 2042-2055 | |
| 17 | Wop Baars | 41 | 2032-2041 | |
| 17 | Drew Cullen | 41 | 2027-2035 | |
| 19 | Manny Guerra# | 40 | 2052-2061 | |
| 20 | Mario Ruíz | 39 | 2023-2031 | |
| 21 | Miguel Cervantes | 38 | 2026-2038 | |
| 21 | Chae-seong Kim | 38 | 2023-2033 | |
| 21 | Giovanni Mireles | 38 | 2026-2045 | |
| 21 | Curt Stokes | 38 | 2053-2059 | |
| 21 | Iwan Vroom# | 38 | 2052-2061 | |
| 26 | Salvador Sagastizabal | 37 | 2036-2043 | |
| 27 | Claudio Díaz | 35 | 2022-2031 | |
| 27 | José Pérez# | 35 | 2051-2060 | |
| 27 | José Salinas | 35 | 2017-2027 | |
| 27 | Andrew Shoemaker | 35 | 2049-2057 | |
| 27 | Javier Soto | 35 | 2040-2044 | |
| 27 | Chin-yau Tu | 35 | 2047-2056 | |
| 33 | Francisco Barrios | 34 | 2020-2033 | |
| 33 | Marvin Mangin | 34 | 2023-2028 | |
| 35 | Miguel Cabañas | 33 | 2029-2035 | |
| 35 | Jeremiah Cole# | 33 | 2051-2057 | |
| 35 | Dan Dunn | 33 | 2042-2047 | |
| 35 | Fred Gunther | 33 | 2036-2040 | |
| 35 | Nick Hayes | 33 | 2041-2047 | |
| 35 | Tsurayaki Tanaka# | 33 | 2051-2060 | |
| 35 | Jing-quo Ts'ai# | 33 | 2052-2056 | |
| 42 | Roy Alsobrook | 32 | 2028-2038 | |
| 42 | Alejandro Araya | 32 | 2028-2039 | |
| 42 | Dennis Brown | 32 | 2022-2030 | |
| 42 | Earl Brown | 32 | 2023-2031 | |
| 42 | Steve Crabtree | 32 | 2053-2057 | |
| 42 | Jimmy Evans | 32 | 2043-2049 | |
| 42 | Antonio Godfrey | 32 | 2028-2033 | |
| 42 | Claude Khatoon | 32 | 2042-2048 | |
| 42 | Steve Sanford | 32 | 2050-2060 | |
| 42 | Shunen Takahashi | 32 | 2022-2035 | |
| 42 | Miguel Álvarez | 32 | 2027-2033 | |
| 53 | Jorge Cedeño | 31 | 2033-2037 | |
| 53 | Steve Costlow | 31 | 2032-2038 | |
| 53 | King Fletcher | 31 | 2023-2030 | |
| 53 | Artie Horton | 31 | 2022-2025 | |
| 53 | Hunter Kirkland | 31 | 2046-2056 | |
| 53 | Hugh Mann# | 31 | 2047-2059 | |
| 53 | Louis McDowell | 31 | 2016-2028 | |
| 53 | Dan McIntyre | 31 | 2049-2056 | |
| 53 | José Ortíz | 31 | 2026-2037 | |
| 53 | Arthur Stevenson | 31 | 2046-2054 | |
| 53 | Larry Strozier | 31 | 2030-2035 | |
| 53 | Joel Walden | 31 | 2036-2043 | |
| 53 | Won-u Yi | 31 | 2029-2041 | |
| 66 | Raúl Andrés | 30 | 2016-2021 | |
| 66 | Edemona Babitu | 30 | 2053-2057 | |
| 66 | Cecil Drabek | 30 | 2043-2051 | |
| 66 | Emerson Horton | 30 | 2039-2044 | |
| 66 | Jason Huggins | 30 | 2037-2046 | |
| 66 | Dahab Kanda | 30 | 2029-2043 | |
| 66 | Raúl Martínez | 30 | 2048-2056 | |
| 66 | Liam Thomson | 30 | 2032-2044 | |
| 66 | Bob Warford | 30 | 2018-2034 | |
| 75 | Lucas Begay | 29 | 2025-2028 | |
| 75 | Roberto Calderón | 29 | 2024-2035 | |
| 75 | Chris Evans | 29 | 2050-2057 | |
| 75 | Arturo Guerrero | 29 | 2028-2039 | |
| 75 | José Guillén | 29 | 2028-2030 | |
| 75 | Roberto Gómez | 29 | 2022-2031 | |
| 75 | Cris Herrera | 29 | 2022-2034 | |
| 75 | John McGrath# | 29 | 2054-2056 | |
| 75 | Sammy Nash | 29 | 2024-2029 | |
| 75 | Scott Thompson | 29 | 2035-2038 | |
| 75 | Mike Thornton | 29 | 2051-2054 | |
| 75 | Octávio Valdéz | 29 | 2033-2039 | |
| 75 | Ed Walters# | 29 | 2049-2057 | |
| 88 | Vince Barnard# | 28 | 2054-2061 | |
| 88 | Frank Bryant | 28 | 2021-2028 | |
| 88 | Benjamin Busto | 28 | 2029-2038 | |
| 88 | Hervé Favier | 28 | 2028-2043 | |
| 88 | Ollie McDaniell | 28 | 2033-2037 | |
| 88 | John Parker# | 28 | 2051-2061 | |
| 88 | Daniel Ricciardo# | 28 | 2051-2061 | |
| 88 | Bobby Roode | 28 | 2031-2041 | |
| 88 | Doug Ryan | 28 | 2016-2024 | |
| 88 | Albert Sierra | 28 | 2034-2041 | |
| 98 | Gary Barber | 27 | 2021-2033 | |
| 98 | Eduardo Capata | 27 | 2019-2032 | |
| 98 | Anthony Carney# | 27 | 2048-2050 |
