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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 | Hakizimana Kipkorir# | 79 | 2047-2057 | |
| 5 | Greg White | 79 | 2015-2028 | |
| 7 | Jon Briddon | 78 | 2022-2032 | |
| 8 | Raúl Fuentes# | 72 | 2048-2055 | |
| 9 | Román Mejía | 71 | 2034-2048 | |
| 10 | Hermenegildo Beliago | 70 | 2027-2044 | |
| 10 | Alexis Zambaco | 70 | 2028-2040 | |
| 12 | Luis Díaz | 69 | 2033-2050 | |
| 12 | Archie MacMurchy# | 69 | 2048-2057 | |
| 14 | Rodrigo García# | 68 | 2047-2057 | |
| 14 | Carlos Sánchez | 68 | 2021-2028 | |
| 16 | Holden Rosen Grupp | 67 | 2030-2042 | |
| 17 | Chip Bishop | 65 | 2015-2030 | |
| 17 | Sexto Rodríguez | 65 | 2015-2025 | |
| 17 | Rod Watts | 65 | 2037-2049 | |
| 20 | Nolan Howard | 64 | 2034-2045 | |
| 20 | Chris Jackson# | 64 | 2048-2057 | |
| 22 | Stewart Telfer# | 63 | 2045-2057 | |
| 22 | Benny York | 63 | 2015-2029 | |
| 24 | Leroy Moody | 62 | 2025-2032 | |
| 25 | Conor Starks# | 61 | 2049-2057 | |
| 26 | Uhi Ahipene# | 60 | 2048-2057 | |
| 26 | Mark Collingwood | 60 | 2031-2041 | |
| 26 | Nick Joseph | 60 | 2043-2056 | |
| 29 | Walt Coffman* | 59 | 2026-2035 | |
| 29 | Armando Romano | 59 | 2033-2038 | |
| 31 | Earl Hurdle | 58 | 2043-2055 | |
| 31 | José Martínez# | 58 | 2050-2054 | |
| 31 | Panda Montana | 58 | 2029-2041 | |
| 34 | Yan van der Meijden | 57 | 2043-2053 | |
| 35 | José Alaniz | 55 | 2016-2030 | |
| 35 | Lou Meadows | 55 | 2016-2029 | |
| 35 | Gerald Orlebar | 55 | 2035-2050 | |
| 38 | Art Adams | 54 | 2021-2030 | |
| 38 | Pat Butler# | 54 | 2044-2056 | |
| 38 | Jordan Calhoun | 54 | 2037-2046 | |
| 38 | Ron Manning | 54 | 2029-2043 | |
| 38 | Jorge Souza# | 54 | 2043-2048 | |
| 43 | John Brown | 52 | 2017-2031 | |
| 43 | Ben Frazier# | 52 | 2050-2057 | |
| 43 | Gunner Hardy | 52 | 2016-2028 | |
| 43 | Cris Herrera | 52 | 2024-2034 | |
| 43 | Zalontae Hillary | 52 | 2031-2038 | |
| 43 | Roman Phansalker | 52 | 2038-2046 | |
| 43 | Pete Rhue | 52 | 2032-2040 | |
| 43 | Chase Sims | 52 | 2038-2048 | |
| 43 | Harry Stuterberg | 52 | 2034-2046 | |
| 52 | Neil Franson | 51 | 2030-2042 | |
| 52 | Hong-bin Hua | 51 | 2040-2046 | |
| 52 | Ernesto López | 51 | 2036-2045 | |
| 52 | Jesús Rosas# | 51 | 2052-2056 | |
| 56 | Nick Long# | 50 | 2049-2056 | |
| 56 | Dan Seymour | 50 | 2042-2054 | |
| 58 | Robbie Betchley | 49 | 2030-2040 | |
| 58 | Dale Hamilton | 49 | 2029-2042 | |
| 60 | Adrián Fierro | 48 | 2020-2034 | |
| 60 | Ryan Peterson | 48 | 2026-2036 | |
| 60 | Addie Samson | 48 | 2024-2034 | |
| 63 | William MacKnight | 47 | 2022-2028 | |
| 64 | George Frazier | 46 | 2017-2037 | |
| 64 | Ken Grant | 46 | 2042-2051 | |
| 64 | Juan Montoya | 46 | 2025-2036 | |
| 64 | Rusty Swanson | 46 | 2026-2035 | |
| 64 | Shunen Takahashi | 46 | 2023-2035 | |
| 69 | Volmer Aalbers# | 45 | 2048-2052 | |
| 69 | Gabriel Durango | 45 | 2039-2049 | |
| 69 | An Jang-Yop* | 45 | 2029-2043 | |
| 69 | Marvin Martin | 45 | 2025-2041 | |
| 69 | Esteban Rodríguez | 45 | 2035-2047 | |
| 74 | John Alvarado | 44 | 2017-2021 | |
| 74 | Mike Bennett | 44 | 2043-2052 | |
| 74 | Woody Carlson | 44 | 2020-2033 | |
| 74 | Paul Haines | 44 | 2038-2051 | |
| 74 | Melvin Haney | 44 | 2023-2030 | |
| 74 | Mal Houser | 44 | 2029-2038 | |
| 74 | Tim Powell | 44 | 2015-2020 | |
| 81 | Edison Larson | 43 | 2020-2039 | |
| 81 | Kevin Nogilny* | 43 | 2031-2046 | |
| 81 | Jesús Ramírez# | 43 | 2050-2056 | |
| 81 | Roderick Rhodes | 43 | 2015-2030 | |
| 85 | António Castillo | 42 | 2027-2038 | |
| 85 | Domingo Ramírez | 42 | 2023-2040 | |
| 85 | Aarre Rissanen# | 42 | 2047-2052 | |
| 85 | Doug Santamarina# | 42 | 2050-2053 | |
| 85 | Quintiliano Seixal | 42 | 2025-2036 | |
| 90 | David Buchanan | 41 | 2029-2043 | |
| 90 | Roberto Calderón | 41 | 2026-2035 | |
| 90 | Dusty Fox | 41 | 2035-2047 | |
| 90 | Doug Green | 41 | 2022-2032 | |
| 90 | Janghyun Han# | 41 | 2045-2057 | |
| 90 | Matt Harris | 41 | 2020-2031 | |
| 90 | Rubén Sánchez# | 41 | 2048-2056 | |
| 90 | Elroy Thompkins | 41 | 2028-2043 | |
| 98 | Bhagavan Antle# | 40 | 2046-2057 | |
| 98 | Alain Arnaud | 40 | 2036-2043 | |
| 98 | Merlin Bassett | 40 | 2029-2038 |
