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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 | 2029-2036 | |
| 4 | Greg White | 79 | 2015-2028 | |
| 5 | Jon Briddon# | 78 | 2022-2032 | |
| 6 | Carlos Sánchez | 68 | 2021-2028 | |
| 7 | Chip Bishop | 65 | 2015-2030 | |
| 7 | Sexto Rodríguez | 65 | 2015-2025 | |
| 9 | Benny York | 63 | 2015-2029 | |
| 10 | Leroy Moody | 62 | 2025-2032 | |
| 11 | Walt Coffman# | 59 | 2026-2035 | |
| 12 | Will Hunting# | 56 | 2030-2036 | |
| 13 | José Alaniz | 55 | 2016-2030 | |
| 13 | Lou Meadows | 55 | 2016-2029 | |
| 13 | Panda Montana# | 55 | 2029-2035 | |
| 13 | Alexis Zambaco# | 55 | 2028-2036 | |
| 17 | Art Adams | 54 | 2021-2030 | |
| 18 | John Brown | 52 | 2017-2031 | |
| 18 | Gunner Hardy | 52 | 2016-2028 | |
| 18 | Cris Herrera# | 52 | 2024-2034 | |
| 21 | Adrián Fierro | 48 | 2020-2034 | |
| 21 | Ryan Peterson# | 48 | 2026-2036 | |
| 21 | Addie Samson# | 48 | 2024-2034 | |
| 24 | William MacKnight | 47 | 2022-2028 | |
| 25 | George Frazier# | 46 | 2017-2032 | |
| 25 | Juan Montoya | 46 | 2025-2036 | |
| 25 | Rusty Swanson# | 46 | 2026-2035 | |
| 25 | Shunen Takahashi | 46 | 2023-2035 | |
| 29 | John Alvarado | 44 | 2017-2021 | |
| 29 | Woody Carlson | 44 | 2020-2033 | |
| 29 | Melvin Haney | 44 | 2023-2030 | |
| 29 | Mal Houser# | 44 | 2029-2036 | |
| 29 | Tim Powell | 44 | 2015-2020 | |
| 34 | Roderick Rhodes | 43 | 2015-2030 | |
| 35 | Armando Romano# | 42 | 2033-2036 | |
| 35 | Quintiliano Seixal# | 42 | 2025-2036 | |
| 37 | Roberto Calderón# | 41 | 2026-2035 | |
| 37 | Neil Franson# | 41 | 2030-2035 | |
| 37 | Doug Green | 41 | 2022-2032 | |
| 37 | Matt Harris | 41 | 2020-2031 | |
| 37 | Ron Manning# | 41 | 2029-2032 | |
| 42 | Jeff Territt | 40 | 2020-2035 | |
| 43 | David Collingwood | 39 | 2018-2031 | |
| 43 | Ronald Harmon | 39 | 2016-2029 | |
| 43 | Edison Larson# | 39 | 2020-2036 | |
| 43 | Pedro Ritodíaz | 39 | 2015-2024 | |
| 47 | Manny Castro# | 38 | 2030-2036 | |
| 47 | Félix Jiménez | 38 | 2022-2026 | |
| 47 | Myles Wilkerson# | 38 | 2026-2033 | |
| 50 | Merlin Bassett# | 37 | 2029-2036 | |
| 50 | David Buchanan# | 37 | 2029-2036 | |
| 50 | Neil Gilliam | 37 | 2021-2026 | |
| 50 | Alfonso Miranda | 37 | 2022-2031 | |
| 50 | Eduardo Molina | 37 | 2022-2033 | |
| 50 | Kevin Nogilny# | 37 | 2031-2035 | |
| 50 | Christian Patrick | 37 | 2019-2028 | |
| 50 | Alfonso Zapata | 37 | 2022-2033 | |
| 58 | Yusuke Chikafuji | 36 | 2024-2032 | |
| 58 | Juan Díaz# | 36 | 2030-2034 | |
| 58 | Kenshin Koike | 36 | 2018-2032 | |
| 58 | Bob Roth# | 36 | 2029-2033 | |
| 62 | Mark Collingwood# | 35 | 2031-2036 | |
| 62 | Jared Cox | 35 | 2016-2022 | |
| 62 | Fernando Padilla# | 35 | 2028-2033 | |
| 62 | Maru Pao Pao# | 35 | 2030-2032 | |
| 62 | Luis Peña# | 35 | 2025-2032 | |
| 62 | Jim Roberts | 35 | 2016-2020 | |
| 62 | Hunter Wilson | 35 | 2022-2027 | |
| 69 | Robbie Betchley# | 34 | 2030-2036 | |
| 69 | Bob Compton | 34 | 2015-2023 | |
| 69 | Jorge Garza | 34 | 2022-2031 | |
| 69 | Il-young Kim | 34 | 2025-2036 | |
| 69 | Dan Mitchell | 34 | 2020-2025 | |
| 69 | Bill Prowse | 34 | 2015-2020 | |
| 75 | Hermenegildo Beliago# | 33 | 2027-2035 | |
| 75 | Ryan Bentley | 33 | 2030-2032 | |
| 75 | Javier Castillo# | 33 | 2024-2036 | |
| 75 | Kent Clement | 33 | 2021-2032 | |
| 75 | Zalontae Hillary# | 33 | 2031-2036 | |
| 75 | Harrison Jones | 33 | 2017-2021 | |
| 75 | Johnny Joyce | 33 | 2015-2019 | |
| 75 | Paul Lowery | 33 | 2015-2020 | |
| 75 | Lorenzo Sánchez | 33 | 2020-2029 | |
| 75 | Dave Stephenson# | 33 | 2029-2035 | |
| 75 | Sukejuro Yokoyama | 33 | 2025-2033 | |
| 86 | Jeff Bradshaw | 32 | 2024-2035 | |
| 86 | Jorge Castillo | 32 | 2020-2030 | |
| 86 | Dale Hamilton# | 32 | 2029-2034 | |
| 86 | Collin Hill | 32 | 2020-2028 | |
| 86 | Clarence Ramsey | 32 | 2017-2022 | |
| 91 | António Castillo# | 31 | 2027-2036 | |
| 91 | Roderick Draper | 31 | 2015-2021 | |
| 91 | Domingo Ramírez# | 31 | 2023-2035 | |
| 91 | Jesús Tejeda | 31 | 2023-2033 | |
| 95 | Mike Jones | 30 | 2016-2020 | |
| 96 | António Cruz | 29 | 2015-2020 | |
| 96 | John Riggleman# | 29 | 2026-2036 | |
| 96 | Chuck Steele | 29 | 2018-2024 | |
| 96 | Yosuke Takahashi | 29 | 2024-2034 | |
| 96 | Luis Torres | 29 | 2024-2032 |
