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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Shigemasa Horiuchi* | 125 | 2017-2031 | |
| 2 | Gary Bailey | 97 | 2015-2032 | |
| 3 | Michael Machen# | 84 | 2029-2041 | |
| 4 | Greg White | 79 | 2015-2028 | |
| 5 | Jon Briddon | 78 | 2022-2032 | |
| 6 | Alexis Zambaco# | 70 | 2028-2040 | |
| 7 | Carlos Sánchez | 68 | 2021-2028 | |
| 8 | Chip Bishop | 65 | 2015-2030 | |
| 8 | Will Hunting# | 65 | 2030-2041 | |
| 8 | Sexto Rodríguez | 65 | 2015-2025 | |
| 11 | Hermenegildo Beliago# | 64 | 2027-2040 | |
| 11 | Nolan Howard# | 64 | 2034-2041 | |
| 13 | Benny York | 63 | 2015-2029 | |
| 14 | Leroy Moody | 62 | 2025-2032 | |
| 15 | Mark Collingwood | 60 | 2031-2041 | |
| 16 | Walt Coffman | 59 | 2026-2035 | |
| 16 | Holden Rosen Grupp# | 59 | 2030-2041 | |
| 16 | Armando Romano# | 59 | 2033-2038 | |
| 19 | Panda Montana# | 58 | 2029-2041 | |
| 20 | José Alaniz | 55 | 2016-2030 | |
| 20 | Lou Meadows | 55 | 2016-2029 | |
| 22 | Art Adams | 54 | 2021-2030 | |
| 23 | John Brown | 52 | 2017-2031 | |
| 23 | Gunner Hardy | 52 | 2016-2028 | |
| 23 | Cris Herrera | 52 | 2024-2034 | |
| 23 | Zalontae Hillary# | 52 | 2031-2038 | |
| 23 | Ron Manning# | 52 | 2029-2041 | |
| 23 | Pete Rhue# | 52 | 2032-2040 | |
| 29 | Robbie Betchley | 49 | 2030-2040 | |
| 29 | Neil Franson# | 49 | 2030-2041 | |
| 31 | Adrián Fierro | 48 | 2020-2034 | |
| 31 | Dale Hamilton# | 48 | 2029-2041 | |
| 31 | Ryan Peterson | 48 | 2026-2036 | |
| 31 | Addie Samson | 48 | 2024-2034 | |
| 35 | William MacKnight | 47 | 2022-2028 | |
| 36 | George Frazier | 46 | 2017-2037 | |
| 36 | Román Mejía# | 46 | 2034-2041 | |
| 36 | Juan Montoya | 46 | 2025-2036 | |
| 36 | Rusty Swanson | 46 | 2026-2035 | |
| 36 | Shunen Takahashi | 46 | 2023-2035 | |
| 41 | Luis Díaz# | 45 | 2033-2041 | |
| 41 | Marvin Martin# | 45 | 2025-2041 | |
| 43 | John Alvarado | 44 | 2017-2021 | |
| 43 | Woody Carlson | 44 | 2020-2033 | |
| 43 | Melvin Haney | 44 | 2023-2030 | |
| 43 | Mal Houser# | 44 | 2029-2038 | |
| 43 | Tim Powell | 44 | 2015-2020 | |
| 48 | Edison Larson | 43 | 2020-2039 | |
| 48 | Roderick Rhodes | 43 | 2015-2030 | |
| 50 | António Castillo | 42 | 2027-2038 | |
| 50 | Domingo Ramírez | 42 | 2023-2040 | |
| 50 | Quintiliano Seixal | 42 | 2025-2036 | |
| 50 | Harry Stuterberg# | 42 | 2034-2040 | |
| 54 | David Buchanan# | 41 | 2029-2040 | |
| 54 | Roberto Calderón | 41 | 2026-2035 | |
| 54 | Doug Green | 41 | 2022-2032 | |
| 54 | Matt Harris | 41 | 2020-2031 | |
| 58 | Merlin Bassett | 40 | 2029-2038 | |
| 58 | Manny Castro | 40 | 2030-2037 | |
| 58 | José Ruíz# | 40 | 2035-2040 | |
| 58 | Jeff Territt | 40 | 2020-2035 | |
| 62 | David Collingwood | 39 | 2018-2031 | |
| 62 | Currito Fonseca# | 39 | 2036-2041 | |
| 62 | Ronald Harmon | 39 | 2016-2029 | |
| 62 | Pedro Ritodíaz | 39 | 2015-2024 | |
| 66 | Félix Jiménez | 38 | 2022-2026 | |
| 66 | John Riggleman | 38 | 2026-2040 | |
| 66 | Myles Wilkerson | 38 | 2026-2033 | |
| 69 | Javier Castillo | 37 | 2024-2040 | |
| 69 | Neil Gilliam | 37 | 2021-2026 | |
| 69 | Alfonso Miranda | 37 | 2022-2031 | |
| 69 | Eduardo Molina | 37 | 2022-2033 | |
| 69 | Kevin Nogilny# | 37 | 2031-2041 | |
| 69 | Maru Pao Pao# | 37 | 2030-2038 | |
| 69 | Christian Patrick | 37 | 2019-2028 | |
| 69 | Esteban Rodríguez# | 37 | 2035-2040 | |
| 69 | Zebulon Vermillion# | 37 | 2038-2041 | |
| 69 | Alfonso Zapata | 37 | 2022-2033 | |
| 79 | Alain Arnaud# | 36 | 2036-2041 | |
| 79 | Yusuke Chikafuji | 36 | 2024-2032 | |
| 79 | Juan Díaz | 36 | 2030-2034 | |
| 79 | Kenshin Koike | 36 | 2018-2032 | |
| 79 | Eddie Kop# | 36 | 2026-2040 | |
| 79 | Ernesto López# | 36 | 2036-2040 | |
| 79 | Bob Roth | 36 | 2029-2033 | |
| 86 | Jared Cox | 35 | 2016-2022 | |
| 86 | Fernando Padilla# | 35 | 2028-2039 | |
| 86 | Luis Peña | 35 | 2025-2032 | |
| 86 | Jim Roberts | 35 | 2016-2020 | |
| 86 | Hunter Wilson | 35 | 2022-2027 | |
| 91 | Bob Compton | 34 | 2015-2023 | |
| 91 | Javier Desdin# | 34 | 2026-2040 | |
| 91 | Jorge Garza | 34 | 2022-2031 | |
| 91 | Il-young Kim | 34 | 2025-2036 | |
| 91 | Dan Mitchell | 34 | 2020-2025 | |
| 91 | Bill Prowse | 34 | 2015-2020 | |
| 91 | Lester Roadley# | 34 | 2036-2041 | |
| 91 | Ángel Rosas# | 34 | 2032-2040 | |
| 91 | Elroy Thompkins# | 34 | 2028-2041 | |
| 91 | Shawn Williams | 34 | 2030-2040 |
