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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Nathaniel Riley | 12 | 2016-2030 | |
| 2 | Bobby Swain | 11 | 2020-2031 | |
| 3 | Pedro Castro | 10 | 2018-2032 | |
| 3 | Wes Hamm | 10 | 2021-2037 | |
| 5 | Andy Coker | 9 | 2016-2026 | |
| 5 | Wayne Craig | 9 | 2015-2023 | |
| 5 | Eddie Kop# | 9 | 2023-2037 | |
| 5 | Allen Yohemas | 9 | 2022-2031 | |
| 9 | Chip Bishop | 8 | 2018-2028 | |
| 9 | Vincent Hall | 8 | 2021-2031 | |
| 9 | Javier Mora | 8 | 2020-2034 | |
| 9 | Juan Torres | 8 | 2021-2032 | |
| 13 | Rafael Cardona | 7 | 2022-2035 | |
| 13 | Cris Mendoza | 7 | 2017-2029 | |
| 13 | Bill Tugwell | 7 | 2029-2034 | |
| 16 | Robbie Baxter# | 6 | 2022-2037 | |
| 16 | Kent Clement | 6 | 2022-2033 | |
| 16 | David Collingwood | 6 | 2019-2028 | |
| 16 | John Dempsey | 6 | 2022-2036 | |
| 16 | Juan Díaz | 6 | 2025-2036 | |
| 16 | Matthew Fallows# | 6 | 2034-2038 | |
| 16 | George Frazier | 6 | 2017-2036 | |
| 16 | Cole Hall | 6 | 2016-2027 | |
| 16 | John Holley | 6 | 2014-2022 | |
| 16 | Anatoly Ivanovich# | 6 | 2030-2038 | |
| 16 | Bartolomeu Lio | 6 | 2019-2034 | |
| 16 | Lou Meadows | 6 | 2016-2027 | |
| 16 | Jorge Otero# | 6 | 2030-2038 | |
| 16 | Roderick Rhodes | 6 | 2017-2028 | |
| 16 | Cory Sanders | 6 | 2021-2036 | |
| 16 | Quintiliano Seixal | 6 | 2025-2037 | |
| 16 | Elroy Thompkins# | 6 | 2029-2037 | |
| 16 | Pedro Valdéz# | 6 | 2020-2037 | |
| 16 | Jesús Vidro# | 6 | 2033-2038 | |
| 35 | Gary Bailey | 5 | 2022-2031 | |
| 35 | John Brown | 5 | 2016-2031 | |
| 35 | Juan Contreras# | 5 | 2030-2038 | |
| 35 | Dorian Daly | 5 | 2028-2036 | |
| 35 | Pablo De La Torre | 5 | 2022-2036 | |
| 35 | Manuel Delgadillo# | 5 | 2028-2038 | |
| 35 | Paul Díaz | 5 | 2019-2030 | |
| 35 | Stewart Fleming | 5 | 2029-2033 | |
| 35 | Jesús Franco | 5 | 2028-2034 | |
| 35 | Raúl Gómez | 5 | 2026-2034 | |
| 35 | Henry Hall | 5 | 2015-2026 | |
| 35 | Wayne Hurst | 5 | 2015-2028 | |
| 35 | Masami Kogawa# | 5 | 2031-2034 | |
| 35 | Edison Larson# | 5 | 2020-2038 | |
| 35 | Raúl Luna# | 5 | 2028-2036 | |
| 35 | Jeff Mahl# | 5 | 2035-2037 | |
| 35 | Francis McBride | 5 | 2023-2027 | |
| 35 | Gerardo Pagán# | 5 | 2027-2036 | |
| 35 | Maru Pao Pao# | 5 | 2029-2037 | |
| 35 | Joe Pruitt# | 5 | 2031-2036 | |
| 35 | Lorenzo Sánchez | 5 | 2020-2033 | |
| 35 | Stanley Yelnats# | 5 | 2030-2038 | |
| 57 | Art Adams | 4 | 2020-2031 | |
| 57 | José Alaniz | 4 | 2020-2030 | |
| 57 | Luqman Barcoo# | 4 | 2032-2035 | |
| 57 | Hermenegildo Beliago# | 4 | 2027-2036 | |
| 57 | Allen Blair | 4 | 2015-2032 | |
| 57 | Kyle Boddy | 4 | 2026-2034 | |
| 57 | Sjaak Bonne# | 4 | 2027-2038 | |
| 57 | Quentin Bowers# | 4 | 2028-2038 | |
| 57 | John Braun | 4 | 2014-2022 | |
| 57 | Billy Crawford | 4 | 2017-2025 | |
| 57 | Joe Crown | 4 | 2015-2026 | |
| 57 | Paul Dudding# | 4 | 2033-2038 | |
| 57 | Adrián Fierro | 4 | 2017-2032 | |
| 57 | Víctor García | 4 | 2023-2036 | |
| 57 | Roger Garrett | 4 | 2014-2024 | |
| 57 | Torvald Geertsen | 4 | 2018-2021 | |
| 57 | Natalino Golaio# | 4 | 2022-2038 | |
| 57 | Ricardo Gómez | 4 | 2023-2032 | |
| 57 | Jesús Gonzáles | 4 | 2020-2031 | |
| 57 | Juan Guillén# | 4 | 2027-2038 | |
| 57 | Jackson Haines | 4 | 2014-2029 | |
| 57 | Jeff Hale | 4 | 2014-2027 | |
| 57 | Russ Horne# | 4 | 2027-2037 | |
| 57 | Félix Jiménez | 4 | 2018-2028 | |
| 57 | Ton Jobse# | 4 | 2031-2037 | |
| 57 | Juan Júlio | 4 | 2018-2026 | |
| 57 | Tetsuzan Kaneko | 4 | 2018-2027 | |
| 57 | Donat Karczmarek# | 4 | 2032-2036 | |
| 57 | Tyler MacHugh | 4 | 2023-2033 | |
| 57 | Stanford McCain# | 4 | 2031-2037 | |
| 57 | Ralph McKinney | 4 | 2019-2034 | |
| 57 | Leroy Moody | 4 | 2025-2033 | |
| 57 | António Muñóz# | 4 | 2029-2037 | |
| 57 | Gordon Neugebauer | 4 | 2025-2032 | |
| 57 | Kevin Nogilny# | 4 | 2032-2037 | |
| 57 | Bill Oulton | 4 | 2021-2033 | |
| 57 | Gustavo Pérez | 4 | 2027-2033 | |
| 57 | José Quiñones# | 4 | 2034-2038 | |
| 57 | Domingo Ramírez# | 4 | 2022-2038 | |
| 57 | Tom Reynolds* | 4 | 2015-2027 | |
| 57 | Armando Romano# | 4 | 2029-2038 | |
| 57 | Addie Samson | 4 | 2023-2035 | |
| 57 | Tony Solíz# | 4 | 2026-2034 | |
| 57 | Eijiro Takahashi | 4 | 2028-2034 |
