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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Carlos Sánchez | 12 | 2021-2028 | |
| 2 | Leslie Brooks | 9 | 2021-2030 | |
| 2 | Shigemasa Horiuchi | 9 | 2017-2031 | |
| 4 | José Alaniz | 8 | 2016-2030 | |
| 5 | Billy Crawford | 7 | 2019-2024 | |
| 5 | Roderick Rhodes | 7 | 2015-2030 | |
| 7 | Gary Bailey | 6 | 2015-2032 | |
| 7 | John Brown | 6 | 2017-2031 | |
| 7 | George Frazier# | 6 | 2017-2037 | |
| 7 | Cris Herrera | 6 | 2024-2034 | |
| 7 | Félix Jiménez | 6 | 2022-2026 | |
| 7 | Edison Larson# | 6 | 2020-2036 | |
| 7 | Keisuke Nishida | 6 | 2027-2031 | |
| 7 | Kevin Nogilny# | 6 | 2031-2035 | |
| 7 | Reynaldo Ortíz | 6 | 2022-2027 | |
| 7 | Armando Romano# | 6 | 2033-2037 | |
| 7 | Greg White | 6 | 2015-2028 | |
| 7 | Alfonso Zapata | 6 | 2022-2033 | |
| 19 | Art Adams | 5 | 2021-2030 | |
| 19 | Faisal bin Nabeel# | 5 | 2032-2037 | |
| 19 | David Buchanan# | 5 | 2029-2037 | |
| 19 | Neil Gilliam | 5 | 2021-2026 | |
| 19 | Toddster Gordo# | 5 | 2029-2030 | |
| 19 | Melvin Haney | 5 | 2023-2030 | |
| 19 | Ronald Harmon | 5 | 2016-2029 | |
| 19 | Michael Machen# | 5 | 2029-2036 | |
| 19 | William MacKnight | 5 | 2022-2028 | |
| 19 | Ron Manning# | 5 | 2029-2037 | |
| 19 | Kazu Omori | 5 | 2030-2034 | |
| 19 | Luis Peña | 5 | 2025-2032 | |
| 19 | Tim Powell | 5 | 2015-2020 | |
| 19 | Myron Snow | 5 | 2015-2025 | |
| 19 | Dave Tomlinson | 5 | 2017-2026 | |
| 19 | Juan Valéncia | 5 | 2023-2024 | |
| 19 | Tomás Vargas# | 5 | 2029-2032 | |
| 19 | Myles Wilkerson | 5 | 2026-2033 | |
| 37 | Chip Bishop | 4 | 2015-2030 | |
| 37 | Rafael Cardona | 4 | 2021-2031 | |
| 37 | António Castillo# | 4 | 2027-2036 | |
| 37 | Jorge Castillo | 4 | 2020-2030 | |
| 37 | Enrique Castro | 4 | 2030-2037 | |
| 37 | David Collingwood | 4 | 2018-2031 | |
| 37 | Javier Desdin# | 4 | 2026-2037 | |
| 37 | Juan Díaz | 4 | 2030-2034 | |
| 37 | Enrique García | 4 | 2024-2030 | |
| 37 | Henry Hall | 4 | 2017-2025 | |
| 37 | Bruce Hamilton | 4 | 2019-2030 | |
| 37 | Zalontae Hillary# | 4 | 2031-2037 | |
| 37 | David Hudson | 4 | 2022-2032 | |
| 37 | Will Hunting# | 4 | 2030-2037 | |
| 37 | Makoto Kato | 4 | 2018-2026 | |
| 37 | Eddie Kop# | 4 | 2026-2037 | |
| 37 | Tyler MacHugh | 4 | 2025-2032 | |
| 37 | Eric Matson# | 4 | 2027-2037 | |
| 37 | Lou Meadows | 4 | 2016-2029 | |
| 37 | Dan Mitchell | 4 | 2020-2025 | |
| 37 | Panda Montana# | 4 | 2029-2035 | |
| 37 | Fernando Padilla# | 4 | 2028-2033 | |
| 37 | Víctor Padilla | 4 | 2017-2020 | |
| 37 | Carlos Ramos | 4 | 2025-2028 | |
| 37 | Jeff Reynolds | 4 | 2018-2020 | |
| 37 | Rafael Rivera# | 4 | 2026-2034 | |
| 37 | Addie Samson | 4 | 2024-2034 | |
| 37 | Jason Starkey# | 4 | 2034-2037 | |
| 65 | Pedro Alejándrez | 3 | 2020-2034 | |
| 65 | John Alvarado | 3 | 2017-2021 | |
| 65 | John Bailey | 3 | 2024-2034 | |
| 65 | Ismael Barrios | 3 | 2024-2026 | |
| 65 | Robbie Betchley# | 3 | 2030-2037 | |
| 65 | Jeff Bradshaw | 3 | 2024-2035 | |
| 65 | Jon Briddon | 3 | 2022-2032 | |
| 65 | Gil Brown# | 3 | 2029-2037 | |
| 65 | Roberto Calderón | 3 | 2026-2035 | |
| 65 | Miguel Castillo | 3 | 2016-2021 | |
| 65 | Kent Clement | 3 | 2021-2032 | |
| 65 | Jared Cox | 3 | 2016-2022 | |
| 65 | Matt Digby# | 3 | 2031-2036 | |
| 65 | Fernando Espinosa | 3 | 2029-2032 | |
| 65 | Lorenzo Fabián# | 3 | 2026-2036 | |
| 65 | Stewart Fleming | 3 | 2031-2031 | |
| 65 | Michael Fletcher | 3 | 2018-2022 | |
| 65 | Jorge Garza | 3 | 2022-2031 | |
| 65 | Darryl Gordon | 3 | 2017-2021 | |
| 65 | Juan Guillén# | 3 | 2026-2037 | |
| 65 | Dale Hamilton# | 3 | 2029-2037 | |
| 65 | Matt Harris | 3 | 2020-2031 | |
| 65 | Gabriel Hidalgo | 3 | 2021-2033 | |
| 65 | Randy Hoffman | 3 | 2017-2024 | |
| 65 | Jessie Holley | 3 | 2015-2021 | |
| 65 | Russ Horne# | 3 | 2024-2036 | |
| 65 | Cal Hudson | 3 | 2017-2019 | |
| 65 | Juan Júlio | 3 | 2015-2026 | |
| 65 | Yeon-kyu Kim# | 3 | 2033-2037 | |
| 65 | Stuart Lee | 3 | 2018-2025 | |
| 65 | Juan Carlos Maestas | 3 | 2015-2024 | |
| 65 | Jeff Mahl# | 3 | 2033-2037 | |
| 65 | Armando Martínez | 3 | 2018-2020 | |
| 65 | Román Mejía# | 3 | 2034-2037 | |
| 65 | Raúl Melro | 3 | 2027-2028 | |
| 65 | Giovanni Mireles# | 3 | 2029-2037 |
