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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 | Will Hunting | 91 | 2030-2044 | |
| 4 | Michael Machen* | 84 | 2029-2041 | |
| 5 | Greg White | 79 | 2015-2028 | |
| 6 | Jon Briddon | 78 | 2022-2032 | |
| 7 | Román Mejía | 71 | 2034-2048 | |
| 8 | Hermenegildo Beliago | 70 | 2027-2044 | |
| 8 | Alexis Zambaco | 70 | 2028-2040 | |
| 10 | Luis Díaz# | 69 | 2033-2050 | |
| 11 | Carlos Sánchez | 68 | 2021-2028 | |
| 12 | Holden Rosen Grupp | 67 | 2030-2042 | |
| 13 | Chip Bishop | 65 | 2015-2030 | |
| 13 | Sexto Rodríguez | 65 | 2015-2025 | |
| 13 | Rod Watts | 65 | 2037-2049 | |
| 16 | Nolan Howard | 64 | 2034-2045 | |
| 17 | Benny York | 63 | 2015-2029 | |
| 18 | Leroy Moody | 62 | 2025-2032 | |
| 19 | Mark Collingwood | 60 | 2031-2041 | |
| 20 | Walt Coffman* | 59 | 2026-2035 | |
| 20 | Armando Romano | 59 | 2033-2038 | |
| 22 | Panda Montana | 58 | 2029-2041 | |
| 23 | José Alaniz | 55 | 2016-2030 | |
| 23 | Lou Meadows | 55 | 2016-2029 | |
| 23 | Gerald Orlebar# | 55 | 2035-2050 | |
| 26 | Art Adams | 54 | 2021-2030 | |
| 26 | Pat Butler# | 54 | 2044-2050 | |
| 26 | Jordan Calhoun# | 54 | 2037-2046 | |
| 26 | Ron Manning | 54 | 2029-2043 | |
| 26 | Jorge Souza# | 54 | 2043-2048 | |
| 31 | John Brown | 52 | 2017-2031 | |
| 31 | Gunner Hardy | 52 | 2016-2028 | |
| 31 | Cris Herrera | 52 | 2024-2034 | |
| 31 | Zalontae Hillary | 52 | 2031-2038 | |
| 31 | Nick Joseph# | 52 | 2043-2050 | |
| 31 | Roman Phansalker | 52 | 2038-2046 | |
| 31 | Pete Rhue | 52 | 2032-2040 | |
| 31 | Chase Sims# | 52 | 2038-2048 | |
| 31 | Harry Stuterberg | 52 | 2034-2046 | |
| 40 | Neil Franson | 51 | 2030-2042 | |
| 40 | Hong-bin Hua | 51 | 2040-2046 | |
| 40 | Ernesto López | 51 | 2036-2045 | |
| 43 | Robbie Betchley | 49 | 2030-2040 | |
| 43 | Dale Hamilton | 49 | 2029-2042 | |
| 45 | Adrián Fierro | 48 | 2020-2034 | |
| 45 | Ryan Peterson | 48 | 2026-2036 | |
| 45 | Addie Samson | 48 | 2024-2034 | |
| 48 | William MacKnight | 47 | 2022-2028 | |
| 48 | Yan van der Meijden# | 47 | 2043-2049 | |
| 50 | George Frazier | 46 | 2017-2037 | |
| 50 | Juan Montoya | 46 | 2025-2036 | |
| 50 | Rusty Swanson | 46 | 2026-2035 | |
| 50 | Shunen Takahashi | 46 | 2023-2035 | |
| 54 | Gabriel Durango# | 45 | 2039-2049 | |
| 54 | An Jang-Yop | 45 | 2029-2043 | |
| 54 | Marvin Martin | 45 | 2025-2041 | |
| 54 | Esteban Rodríguez | 45 | 2035-2047 | |
| 58 | John Alvarado | 44 | 2017-2021 | |
| 58 | Woody Carlson | 44 | 2020-2033 | |
| 58 | Melvin Haney | 44 | 2023-2030 | |
| 58 | Mal Houser | 44 | 2029-2038 | |
| 58 | Tim Powell | 44 | 2015-2020 | |
| 63 | Ken Grant# | 43 | 2042-2050 | |
| 63 | Edison Larson | 43 | 2020-2039 | |
| 63 | Kevin Nogilny | 43 | 2031-2046 | |
| 63 | Roderick Rhodes | 43 | 2015-2030 | |
| 67 | António Castillo | 42 | 2027-2038 | |
| 67 | Domingo Ramírez | 42 | 2023-2040 | |
| 67 | Quintiliano Seixal | 42 | 2025-2036 | |
| 70 | David Buchanan | 41 | 2029-2043 | |
| 70 | Roberto Calderón | 41 | 2026-2035 | |
| 70 | Dusty Fox | 41 | 2035-2047 | |
| 70 | Doug Green | 41 | 2022-2032 | |
| 70 | Matt Harris | 41 | 2020-2031 | |
| 70 | Elroy Thompkins | 41 | 2028-2043 | |
| 76 | Alain Arnaud | 40 | 2036-2043 | |
| 76 | Merlin Bassett | 40 | 2029-2038 | |
| 76 | Kjeld Burger# | 40 | 2046-2050 | |
| 76 | Manny Castro | 40 | 2030-2037 | |
| 76 | Javier Desdin | 40 | 2026-2043 | |
| 76 | Ton Jobse | 40 | 2036-2045 | |
| 76 | Jared LaBarge# | 40 | 2040-2050 | |
| 76 | José Ruíz | 40 | 2035-2040 | |
| 76 | Jeff Territt | 40 | 2020-2035 | |
| 85 | David Collingwood | 39 | 2018-2031 | |
| 85 | Currito Fonseca# | 39 | 2036-2046 | |
| 85 | Ronald Harmon | 39 | 2016-2029 | |
| 85 | Pedro Ritodíaz | 39 | 2015-2024 | |
| 89 | Bob Hollingsworth# | 38 | 2043-2049 | |
| 89 | Félix Jiménez | 38 | 2022-2026 | |
| 89 | Eddie Kop* | 38 | 2026-2042 | |
| 89 | John Riggleman | 38 | 2026-2040 | |
| 89 | Ricky Sellers | 38 | 2039-2043 | |
| 89 | Myles Wilkerson | 38 | 2026-2033 | |
| 95 | Lance Barber# | 37 | 2040-2046 | |
| 95 | Javier Castillo | 37 | 2024-2040 | |
| 95 | Neil Gilliam | 37 | 2021-2026 | |
| 95 | Alan Halsall# | 37 | 2042-2050 | |
| 95 | Alfonso Miranda | 37 | 2022-2031 | |
| 95 | Eduardo Molina | 37 | 2022-2033 |
