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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 | |
| 4 | Armando Romano# | 8 | 2033-2038 | |
| 6 | Billy Crawford | 7 | 2019-2024 | |
| 6 | Edison Larson | 7 | 2020-2039 | |
| 6 | Kevin Nogilny# | 7 | 2031-2041 | |
| 6 | Roderick Rhodes | 7 | 2015-2030 | |
| 10 | Gary Bailey | 6 | 2015-2032 | |
| 10 | Faisal bin Nabeel# | 6 | 2032-2041 | |
| 10 | John Brown | 6 | 2017-2031 | |
| 10 | George Frazier | 6 | 2017-2037 | |
| 10 | Cris Herrera | 6 | 2024-2034 | |
| 10 | Zalontae Hillary# | 6 | 2031-2038 | |
| 10 | Félix Jiménez | 6 | 2022-2026 | |
| 10 | Keisuke Nishida | 6 | 2027-2031 | |
| 10 | Reynaldo Ortíz | 6 | 2022-2027 | |
| 10 | Greg White | 6 | 2015-2028 | |
| 10 | Markus Widner# | 6 | 2034-2042 | |
| 10 | Alfonso Zapata | 6 | 2022-2033 | |
| 22 | Art Adams | 5 | 2021-2030 | |
| 22 | David Buchanan# | 5 | 2029-2040 | |
| 22 | António Castillo | 5 | 2027-2038 | |
| 22 | Neil Gilliam | 5 | 2021-2026 | |
| 22 | Toddster Gordo | 5 | 2029-2038 | |
| 22 | Melvin Haney | 5 | 2023-2030 | |
| 22 | Ronald Harmon | 5 | 2016-2029 | |
| 22 | Will Hunting# | 5 | 2030-2042 | |
| 22 | Michael Machen | 5 | 2029-2041 | |
| 22 | William MacKnight | 5 | 2022-2028 | |
| 22 | Ron Manning# | 5 | 2029-2042 | |
| 22 | Jeffery Meyers# | 5 | 2038-2042 | |
| 22 | Kazu Omori | 5 | 2030-2034 | |
| 22 | Luis Peña | 5 | 2025-2032 | |
| 22 | Tim Powell | 5 | 2015-2020 | |
| 22 | Myron Snow | 5 | 2015-2025 | |
| 22 | Dave Tomlinson | 5 | 2017-2026 | |
| 22 | Juan Valéncia | 5 | 2023-2024 | |
| 22 | Tomás Vargas | 5 | 2029-2032 | |
| 22 | Myles Wilkerson | 5 | 2026-2033 | |
| 42 | Robbie Betchley | 4 | 2030-2040 | |
| 42 | Chip Bishop | 4 | 2015-2030 | |
| 42 | Rafael Cardona | 4 | 2021-2031 | |
| 42 | Jorge Castillo | 4 | 2020-2030 | |
| 42 | Enrique Castro | 4 | 2030-2037 | |
| 42 | Cliff Claven# | 4 | 2035-2042 | |
| 42 | David Collingwood | 4 | 2018-2031 | |
| 42 | Javier Desdin# | 4 | 2026-2042 | |
| 42 | Juan Díaz | 4 | 2030-2034 | |
| 42 | Craig Fitzgerald# | 4 | 2039-2042 | |
| 42 | Enrique García | 4 | 2024-2030 | |
| 42 | Henry Hall | 4 | 2017-2025 | |
| 42 | Bruce Hamilton | 4 | 2019-2030 | |
| 42 | Dale Hamilton# | 4 | 2029-2042 | |
| 42 | Chris Holland# | 4 | 2034-2042 | |
| 42 | David Hudson | 4 | 2022-2032 | |
| 42 | Makoto Kato | 4 | 2018-2026 | |
| 42 | Yeon-kyu Kim | 4 | 2033-2040 | |
| 42 | Eddie Kop | 4 | 2026-2042 | |
| 42 | Tyler MacHugh | 4 | 2025-2032 | |
| 42 | Eric Matson | 4 | 2027-2040 | |
| 42 | Lou Meadows | 4 | 2016-2029 | |
| 42 | Dan Mitchell | 4 | 2020-2025 | |
| 42 | Panda Montana | 4 | 2029-2041 | |
| 42 | Yajirobei Otomo | 4 | 2029-2038 | |
| 42 | Fernando Padilla | 4 | 2028-2039 | |
| 42 | Víctor Padilla | 4 | 2017-2020 | |
| 42 | Carlos Ramos | 4 | 2025-2028 | |
| 42 | Jeff Reynolds | 4 | 2018-2020 | |
| 42 | John Riggleman | 4 | 2026-2040 | |
| 42 | Rafael Rivera | 4 | 2026-2040 | |
| 42 | Addie Samson | 4 | 2024-2034 | |
| 42 | Ricky Sellers# | 4 | 2039-2042 | |
| 42 | Jason Starkey# | 4 | 2034-2041 | |
| 42 | Leon von Stroheim | 4 | 2034-2040 | |
| 42 | Brantford Winstworth III# | 4 | 2030-2042 | |
| 78 | Pedro Alejándrez* | 3 | 2020-2034 | |
| 78 | John Alvarado | 3 | 2017-2021 | |
| 78 | Alain Arnaud# | 3 | 2036-2042 | |
| 78 | John Bailey | 3 | 2024-2034 | |
| 78 | Ismael Barrios | 3 | 2024-2026 | |
| 78 | Tate Beason# | 3 | 2030-2042 | |
| 78 | Sjaak Bonne | 3 | 2024-2040 | |
| 78 | Jeff Bradshaw | 3 | 2024-2035 | |
| 78 | Jon Briddon | 3 | 2022-2032 | |
| 78 | Gil Brown | 3 | 2029-2038 | |
| 78 | Roberto Calderón | 3 | 2026-2035 | |
| 78 | Jordan Calhoun# | 3 | 2037-2042 | |
| 78 | Miguel Castillo | 3 | 2016-2021 | |
| 78 | Kent Clement | 3 | 2021-2032 | |
| 78 | Jordan Coffey# | 3 | 2037-2042 | |
| 78 | Juan Contreras# | 3 | 2033-2040 | |
| 78 | Jared Cox | 3 | 2016-2022 | |
| 78 | Matt Digby# | 3 | 2031-2040 | |
| 78 | Matt Dunn# | 3 | 2039-2042 | |
| 78 | Fernando Espinosa | 3 | 2029-2032 | |
| 78 | Lorenzo Fabián | 3 | 2026-2036 | |
| 78 | Stewart Fleming | 3 | 2031-2031 | |
| 78 | Michael Fletcher | 3 | 2018-2022 |
