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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 | Greg White | 79 | 2015-2028 | |
| 4 | Jon Briddon# | 78 | 2022-2032 | |
| 5 | Carlos Sánchez# | 68 | 2021-2028 | |
| 6 | Chip Bishop | 65 | 2015-2030 | |
| 6 | Sexto Rodríguez | 65 | 2015-2025 | |
| 8 | Benny York | 63 | 2015-2029 | |
| 9 | Leroy Moody# | 62 | 2025-2032 | |
| 10 | José Alaniz# | 55 | 2016-2030 | |
| 10 | Lou Meadows | 55 | 2016-2029 | |
| 12 | Art Adams# | 54 | 2021-2030 | |
| 13 | John Brown | 52 | 2017-2031 | |
| 13 | Gunner Hardy | 52 | 2016-2028 | |
| 15 | Cris Herrera# | 51 | 2024-2032 | |
| 16 | Walt Coffman# | 48 | 2026-2029 | |
| 16 | Addie Samson# | 48 | 2024-2027 | |
| 18 | William MacKnight# | 47 | 2022-2028 | |
| 19 | George Frazier# | 46 | 2017-2032 | |
| 20 | Shunen Takahashi# | 45 | 2023-2030 | |
| 21 | John Alvarado | 44 | 2017-2021 | |
| 21 | Melvin Haney# | 44 | 2023-2030 | |
| 21 | Tim Powell | 44 | 2015-2020 | |
| 24 | Woody Carlson# | 43 | 2020-2032 | |
| 24 | Adrián Fierro# | 43 | 2020-2032 | |
| 24 | Juan Montoya# | 43 | 2025-2031 | |
| 24 | Roderick Rhodes | 43 | 2015-2030 | |
| 28 | Doug Green# | 41 | 2022-2032 | |
| 28 | Matt Harris | 41 | 2020-2031 | |
| 28 | Ron Manning# | 41 | 2029-2032 | |
| 28 | Ryan Peterson# | 41 | 2026-2030 | |
| 32 | David Collingwood# | 39 | 2018-2031 | |
| 32 | Ronald Harmon | 39 | 2016-2029 | |
| 32 | Pedro Ritodíaz | 39 | 2015-2024 | |
| 35 | Félix Jiménez | 38 | 2022-2026 | |
| 35 | Michael Machen# | 38 | 2029-2032 | |
| 35 | Jeff Territt# | 38 | 2020-2030 | |
| 35 | Alexis Zambaco# | 38 | 2028-2032 | |
| 39 | David Buchanan# | 37 | 2029-2032 | |
| 39 | Neil Gilliam | 37 | 2021-2026 | |
| 39 | Alfonso Miranda# | 37 | 2022-2031 | |
| 39 | Eduardo Molina# | 37 | 2022-2025 | |
| 39 | Christian Patrick | 37 | 2019-2028 | |
| 39 | Myles Wilkerson# | 37 | 2026-2032 | |
| 39 | Alfonso Zapata# | 37 | 2022-2025 | |
| 46 | Yusuke Chikafuji# | 36 | 2024-2032 | |
| 46 | Kenshin Koike | 36 | 2018-2032 | |
| 48 | Roberto Calderón# | 35 | 2026-2032 | |
| 48 | Jared Cox | 35 | 2016-2022 | |
| 48 | Maru Pao Pao# | 35 | 2030-2032 | |
| 48 | Luis Peña# | 35 | 2025-2032 | |
| 48 | Jim Roberts | 35 | 2016-2020 | |
| 48 | Rusty Swanson# | 35 | 2026-2029 | |
| 48 | Hunter Wilson | 35 | 2022-2027 | |
| 55 | Bob Compton | 34 | 2015-2023 | |
| 55 | Jorge Garza# | 34 | 2022-2031 | |
| 55 | Dan Mitchell# | 34 | 2020-2025 | |
| 55 | Bill Prowse | 34 | 2015-2020 | |
| 59 | Ryan Bentley# | 33 | 2030-2032 | |
| 59 | Kent Clement# | 33 | 2021-2032 | |
| 59 | Mal Houser# | 33 | 2029-2032 | |
| 59 | Harrison Jones | 33 | 2017-2021 | |
| 59 | Johnny Joyce | 33 | 2015-2019 | |
| 59 | Paul Lowery | 33 | 2015-2020 | |
| 59 | Lorenzo Sánchez# | 33 | 2020-2029 | |
| 66 | Jeff Bradshaw# | 32 | 2024-2030 | |
| 66 | Jorge Castillo | 32 | 2020-2030 | |
| 66 | Dale Hamilton# | 32 | 2029-2032 | |
| 66 | Collin Hill# | 32 | 2020-2028 | |
| 66 | Clarence Ramsey | 32 | 2017-2022 | |
| 66 | Quintiliano Seixal# | 32 | 2025-2032 | |
| 72 | Hermenegildo Beliago# | 31 | 2027-2030 | |
| 72 | António Castillo# | 31 | 2027-2032 | |
| 72 | Javier Castillo# | 31 | 2024-2032 | |
| 72 | Roderick Draper | 31 | 2015-2021 | |
| 72 | Edison Larson# | 31 | 2020-2029 | |
| 72 | Panda Montana# | 31 | 2029-2032 | |
| 78 | Mike Jones | 30 | 2016-2020 | |
| 78 | Il-young Kim# | 30 | 2025-2032 | |
| 78 | Jesús Tejeda# | 30 | 2023-2032 | |
| 78 | Sukejuro Yokoyama# | 30 | 2025-2032 | |
| 82 | António Cruz | 29 | 2015-2020 | |
| 82 | Chuck Steele | 29 | 2018-2024 | |
| 82 | Luis Torres# | 29 | 2024-2032 | |
| 85 | Quentin Bowers# | 28 | 2027-2032 | |
| 85 | Rafael Cardona# | 28 | 2021-2031 | |
| 85 | Esteban Costello | 28 | 2018-2021 | |
| 85 | Cisco Cruz | 28 | 2017-2025 | |
| 85 | Pat Farrell | 28 | 2015-2023 | |
| 85 | Roger Garrett | 28 | 2016-2024 | |
| 85 | Guillermo Pérez | 28 | 2017-2025 | |
| 85 | Bob Roth# | 28 | 2029-2032 | |
| 85 | Yosuke Takahashi# | 28 | 2024-2032 | |
| 94 | Kent Hubbard | 27 | 2015-2020 | |
| 94 | Javier Ramírez | 27 | 2018-2026 | |
| 94 | José Rico# | 27 | 2025-2032 | |
| 94 | Bobby Swain# | 27 | 2024-2032 | |
| 94 | Tomás Vargas# | 27 | 2029-2032 | |
| 99 | Elvin Brooks | 26 | 2017-2028 | |
| 99 | Leslie Brooks | 26 | 2021-2030 |
