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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 | |
| 5 | Will Hunting# | 78 | 2030-2042 | |
| 7 | Alexis Zambaco# | 70 | 2028-2040 | |
| 8 | Hermenegildo Beliago# | 68 | 2027-2042 | |
| 8 | Carlos Sánchez | 68 | 2021-2028 | |
| 10 | Holden Rosen Grupp# | 67 | 2030-2042 | |
| 11 | Chip Bishop | 65 | 2015-2030 | |
| 11 | Sexto Rodríguez | 65 | 2015-2025 | |
| 13 | Nolan Howard# | 64 | 2034-2041 | |
| 14 | Benny York | 63 | 2015-2029 | |
| 15 | Leroy Moody | 62 | 2025-2032 | |
| 16 | Mark Collingwood | 60 | 2031-2041 | |
| 17 | Walt Coffman | 59 | 2026-2035 | |
| 17 | Armando Romano# | 59 | 2033-2038 | |
| 19 | Panda Montana | 58 | 2029-2041 | |
| 20 | Luis Díaz# | 56 | 2033-2042 | |
| 21 | José Alaniz | 55 | 2016-2030 | |
| 21 | Lou Meadows | 55 | 2016-2029 | |
| 23 | Art Adams | 54 | 2021-2030 | |
| 23 | Ron Manning# | 54 | 2029-2042 | |
| 25 | John Brown | 52 | 2017-2031 | |
| 25 | Gunner Hardy | 52 | 2016-2028 | |
| 25 | Cris Herrera | 52 | 2024-2034 | |
| 25 | Zalontae Hillary# | 52 | 2031-2038 | |
| 25 | Pete Rhue# | 52 | 2032-2040 | |
| 30 | Neil Franson | 51 | 2030-2042 | |
| 31 | Robbie Betchley | 49 | 2030-2040 | |
| 31 | Dale Hamilton# | 49 | 2029-2042 | |
| 33 | Adrián Fierro | 48 | 2020-2034 | |
| 33 | Román Mejía# | 48 | 2034-2042 | |
| 33 | Ryan Peterson | 48 | 2026-2036 | |
| 33 | Addie Samson | 48 | 2024-2034 | |
| 37 | William MacKnight | 47 | 2022-2028 | |
| 38 | George Frazier | 46 | 2017-2037 | |
| 38 | Juan Montoya | 46 | 2025-2036 | |
| 38 | Rusty Swanson | 46 | 2026-2035 | |
| 38 | Shunen Takahashi | 46 | 2023-2035 | |
| 42 | 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 | |
| 58 | Elroy Thompkins# | 40 | 2028-2042 | |
| 63 | Alain Arnaud# | 39 | 2036-2042 | |
| 63 | David Collingwood | 39 | 2018-2031 | |
| 63 | Currito Fonseca# | 39 | 2036-2041 | |
| 63 | Ronald Harmon | 39 | 2016-2029 | |
| 63 | Pedro Ritodíaz | 39 | 2015-2024 | |
| 68 | Félix Jiménez | 38 | 2022-2026 | |
| 68 | Eddie Kop | 38 | 2026-2042 | |
| 68 | John Riggleman | 38 | 2026-2040 | |
| 68 | Rod Watts# | 38 | 2037-2042 | |
| 68 | Myles Wilkerson | 38 | 2026-2033 | |
| 73 | Javier Castillo | 37 | 2024-2040 | |
| 73 | Javier Desdin# | 37 | 2026-2042 | |
| 73 | Neil Gilliam | 37 | 2021-2026 | |
| 73 | Alfonso Miranda | 37 | 2022-2031 | |
| 73 | Eduardo Molina | 37 | 2022-2033 | |
| 73 | Kevin Nogilny# | 37 | 2031-2041 | |
| 73 | Maru Pao Pao# | 37 | 2030-2038 | |
| 73 | Christian Patrick | 37 | 2019-2028 | |
| 73 | Esteban Rodríguez# | 37 | 2035-2040 | |
| 73 | Zebulon Vermillion# | 37 | 2038-2041 | |
| 73 | Alfonso Zapata | 37 | 2022-2033 | |
| 84 | Yusuke Chikafuji | 36 | 2024-2032 | |
| 84 | Juan Díaz | 36 | 2030-2034 | |
| 84 | Kenshin Koike | 36 | 2018-2032 | |
| 84 | Ernesto López# | 36 | 2036-2040 | |
| 84 | Roman Phansalker# | 36 | 2038-2042 | |
| 84 | Bob Roth | 36 | 2029-2033 | |
| 90 | Jared Cox | 35 | 2016-2022 | |
| 90 | Fernando Padilla | 35 | 2028-2039 | |
| 90 | Luis Peña | 35 | 2025-2032 | |
| 90 | Jim Roberts | 35 | 2016-2020 | |
| 90 | Hunter Wilson | 35 | 2022-2027 | |
| 95 | Bob Compton | 34 | 2015-2023 | |
| 95 | Dusty Fox# | 34 | 2035-2042 | |
| 95 | Jorge Garza | 34 | 2022-2031 | |
| 95 | Il-young Kim | 34 | 2025-2036 | |
| 95 | Dan Mitchell | 34 | 2020-2025 | |
| 95 | Bill Prowse | 34 | 2015-2020 |
