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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 | Will Hunting# | 62 | 2030-2037 | |
| 10 | Leroy Moody | 62 | 2025-2032 | |
| 12 | Walt Coffman# | 59 | 2026-2035 | |
| 13 | José Alaniz | 55 | 2016-2030 | |
| 13 | Lou Meadows | 55 | 2016-2029 | |
| 13 | Panda Montana# | 55 | 2029-2035 | |
| 13 | Alexis Zambaco# | 55 | 2028-2037 | |
| 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 | Armando Romano# | 49 | 2033-2037 | |
| 22 | Adrián Fierro | 48 | 2020-2034 | |
| 22 | Ryan Peterson# | 48 | 2026-2036 | |
| 22 | Addie Samson | 48 | 2024-2034 | |
| 25 | William MacKnight | 47 | 2022-2028 | |
| 26 | George Frazier# | 46 | 2017-2037 | |
| 26 | Juan Montoya | 46 | 2025-2036 | |
| 26 | Rusty Swanson# | 46 | 2026-2035 | |
| 26 | Shunen Takahashi | 46 | 2023-2035 | |
| 30 | John Alvarado | 44 | 2017-2021 | |
| 30 | Woody Carlson | 44 | 2020-2033 | |
| 30 | Melvin Haney | 44 | 2023-2030 | |
| 30 | Mal Houser# | 44 | 2029-2036 | |
| 30 | Tim Powell | 44 | 2015-2020 | |
| 35 | Roderick Rhodes | 43 | 2015-2030 | |
| 36 | Zalontae Hillary# | 42 | 2031-2037 | |
| 36 | Ron Manning# | 42 | 2029-2037 | |
| 36 | Quintiliano Seixal | 42 | 2025-2036 | |
| 39 | David Buchanan# | 41 | 2029-2037 | |
| 39 | Roberto Calderón | 41 | 2026-2035 | |
| 39 | Neil Franson# | 41 | 2030-2035 | |
| 39 | Doug Green | 41 | 2022-2032 | |
| 39 | Matt Harris | 41 | 2020-2031 | |
| 44 | Robbie Betchley# | 40 | 2030-2037 | |
| 44 | Manny Castro# | 40 | 2030-2037 | |
| 44 | Mark Collingwood# | 40 | 2031-2037 | |
| 44 | Jeff Territt | 40 | 2020-2035 | |
| 48 | David Collingwood | 39 | 2018-2031 | |
| 48 | Ronald Harmon | 39 | 2016-2029 | |
| 48 | Edison Larson# | 39 | 2020-2036 | |
| 48 | Pedro Ritodíaz | 39 | 2015-2024 | |
| 52 | Félix Jiménez | 38 | 2022-2026 | |
| 52 | Myles Wilkerson | 38 | 2026-2033 | |
| 54 | Merlin Bassett# | 37 | 2029-2036 | |
| 54 | Hermenegildo Beliago# | 37 | 2027-2037 | |
| 54 | Neil Gilliam | 37 | 2021-2026 | |
| 54 | Alfonso Miranda | 37 | 2022-2031 | |
| 54 | Eduardo Molina | 37 | 2022-2033 | |
| 54 | Kevin Nogilny# | 37 | 2031-2035 | |
| 54 | Christian Patrick | 37 | 2019-2028 | |
| 54 | Alfonso Zapata | 37 | 2022-2033 | |
| 62 | Yusuke Chikafuji | 36 | 2024-2032 | |
| 62 | Juan Díaz | 36 | 2030-2034 | |
| 62 | Kenshin Koike | 36 | 2018-2032 | |
| 62 | Bob Roth# | 36 | 2029-2033 | |
| 66 | Jared Cox | 35 | 2016-2022 | |
| 66 | Fernando Padilla# | 35 | 2028-2033 | |
| 66 | Maru Pao Pao# | 35 | 2030-2032 | |
| 66 | Luis Peña | 35 | 2025-2032 | |
| 66 | Jim Roberts | 35 | 2016-2020 | |
| 66 | Hunter Wilson | 35 | 2022-2027 | |
| 72 | Bob Compton | 34 | 2015-2023 | |
| 72 | Jorge Garza | 34 | 2022-2031 | |
| 72 | Il-young Kim | 34 | 2025-2036 | |
| 72 | Dan Mitchell | 34 | 2020-2025 | |
| 72 | Bill Prowse | 34 | 2015-2020 | |
| 77 | Ryan Bentley | 33 | 2030-2032 | |
| 77 | Quentin Bowers# | 33 | 2027-2037 | |
| 77 | Javier Castillo# | 33 | 2024-2036 | |
| 77 | Kent Clement | 33 | 2021-2032 | |
| 77 | Harrison Jones | 33 | 2017-2021 | |
| 77 | Johnny Joyce | 33 | 2015-2019 | |
| 77 | Paul Lowery | 33 | 2015-2020 | |
| 77 | Lorenzo Sánchez | 33 | 2020-2029 | |
| 77 | Dave Stephenson# | 33 | 2029-2035 | |
| 77 | Sukejuro Yokoyama | 33 | 2025-2033 | |
| 87 | Jeff Bradshaw | 32 | 2024-2035 | |
| 87 | Jorge Castillo | 32 | 2020-2030 | |
| 87 | Dale Hamilton# | 32 | 2029-2037 | |
| 87 | Collin Hill | 32 | 2020-2028 | |
| 87 | Clarence Ramsey | 32 | 2017-2022 | |
| 92 | António Castillo# | 31 | 2027-2036 | |
| 92 | Roderick Draper | 31 | 2015-2021 | |
| 92 | Eddie Kop# | 31 | 2026-2037 | |
| 92 | Domingo Ramírez# | 31 | 2023-2035 | |
| 92 | Pete Rhue# | 31 | 2032-2037 | |
| 92 | Jesús Tejeda | 31 | 2023-2033 | |
| 98 | Luis Díaz# | 30 | 2033-2037 | |
| 98 | Dusty Fox# | 30 | 2035-2037 | |
| 98 | Mike Jones | 30 | 2016-2020 |
