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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 | Pat Butler# | 7 | 2044-2050 | |
| 6 | Billy Crawford | 7 | 2019-2024 | |
| 6 | Edison Larson | 7 | 2020-2039 | |
| 6 | Kevin Nogilny | 7 | 2031-2046 | |
| 6 | Roderick Rhodes | 7 | 2015-2030 | |
| 6 | Jaganmani Vivek | 7 | 2041-2046 | |
| 6 | Markus Widner | 7 | 2034-2045 | |
| 13 | Gary Bailey* | 6 | 2015-2032 | |
| 13 | Faisal bin Nabeel | 6 | 2032-2041 | |
| 13 | John Brown | 6 | 2017-2031 | |
| 13 | Jordan Calhoun# | 6 | 2037-2046 | |
| 13 | Dan Dunn# | 6 | 2043-2050 | |
| 13 | George Frazier | 6 | 2017-2037 | |
| 13 | Cris Herrera | 6 | 2024-2034 | |
| 13 | Zalontae Hillary | 6 | 2031-2038 | |
| 13 | Will Hunting | 6 | 2030-2044 | |
| 13 | Félix Jiménez | 6 | 2022-2026 | |
| 13 | Johnny Jones# | 6 | 2042-2050 | |
| 13 | Keisuke Nishida | 6 | 2027-2031 | |
| 13 | Reynaldo Ortíz | 6 | 2022-2027 | |
| 13 | Jason Starkey | 6 | 2034-2048 | |
| 13 | Greg White | 6 | 2015-2028 | |
| 13 | Alfonso Zapata | 6 | 2022-2033 | |
| 29 | Art Adams | 5 | 2021-2030 | |
| 29 | Lance Barber# | 5 | 2040-2046 | |
| 29 | Mike Bennett# | 5 | 2043-2049 | |
| 29 | David Buchanan | 5 | 2029-2043 | |
| 29 | Alfonso Caballero# | 5 | 2038-2050 | |
| 29 | António Castillo | 5 | 2027-2038 | |
| 29 | Gabriel Durango# | 5 | 2039-2049 | |
| 29 | Craig Fitzgerald | 5 | 2039-2043 | |
| 29 | Neil Gilliam | 5 | 2021-2026 | |
| 29 | Toddster Gordo | 5 | 2029-2038 | |
| 29 | Melvin Haney | 5 | 2023-2030 | |
| 29 | Ronald Harmon | 5 | 2016-2029 | |
| 29 | Chris Holland | 5 | 2034-2043 | |
| 29 | Michael Machen* | 5 | 2029-2041 | |
| 29 | William MacKnight | 5 | 2022-2028 | |
| 29 | Archie MacMurchy# | 5 | 2048-2050 | |
| 29 | Ron Manning | 5 | 2029-2043 | |
| 29 | Jeffery Meyers# | 5 | 2038-2043 | |
| 29 | Kazu Omori | 5 | 2030-2034 | |
| 29 | Luis Peña | 5 | 2025-2032 | |
| 29 | Roman Phansalker | 5 | 2038-2046 | |
| 29 | Tim Powell | 5 | 2015-2020 | |
| 29 | Ricky Sellers | 5 | 2039-2043 | |
| 29 | Chase Sims# | 5 | 2038-2048 | |
| 29 | Myron Snow | 5 | 2015-2025 | |
| 29 | Dave Tomlinson | 5 | 2017-2026 | |
| 29 | Juan Valéncia | 5 | 2023-2024 | |
| 29 | Yan van der Meijden# | 5 | 2043-2049 | |
| 29 | Tomás Vargas | 5 | 2029-2032 | |
| 29 | Myles Wilkerson | 5 | 2026-2033 | |
| 59 | Nick Altrock# | 4 | 2039-2046 | |
| 59 | Robbie Betchley | 4 | 2030-2040 | |
| 59 | Chip Bishop | 4 | 2015-2030 | |
| 59 | Rafael Cardona | 4 | 2021-2031 | |
| 59 | Jorge Castillo | 4 | 2020-2030 | |
| 59 | Enrique Castro | 4 | 2030-2037 | |
| 59 | Cliff Claven | 4 | 2035-2045 | |
| 59 | David Collingwood | 4 | 2018-2031 | |
| 59 | Javier Desdin | 4 | 2026-2043 | |
| 59 | Juan Díaz | 4 | 2030-2034 | |
| 59 | Enrique García | 4 | 2024-2030 | |
| 59 | Ken Grant# | 4 | 2042-2050 | |
| 59 | Henry Hall | 4 | 2017-2025 | |
| 59 | Bruce Hamilton | 4 | 2019-2030 | |
| 59 | Dale Hamilton | 4 | 2029-2042 | |
| 59 | Janghyun Han# | 4 | 2045-2047 | |
| 59 | Corbin Holling | 4 | 2034-2045 | |
| 59 | David Hudson | 4 | 2022-2032 | |
| 59 | Earl Hurdle# | 4 | 2043-2050 | |
| 59 | Makoto Kato | 4 | 2018-2026 | |
| 59 | Yeon-kyu Kim | 4 | 2033-2040 | |
| 59 | Eddie Kop* | 4 | 2026-2042 | |
| 59 | Jared LaBarge# | 4 | 2040-2050 | |
| 59 | Tyler MacHugh | 4 | 2025-2032 | |
| 59 | Eric Matson* | 4 | 2027-2040 | |
| 59 | Lou Meadows | 4 | 2016-2029 | |
| 59 | Giovanni Mireles | 4 | 2029-2043 | |
| 59 | Dan Mitchell | 4 | 2020-2025 | |
| 59 | Panda Montana | 4 | 2029-2041 | |
| 59 | Gerald Orlebar# | 4 | 2035-2050 | |
| 59 | Yajirobei Otomo | 4 | 2029-2038 | |
| 59 | Fernando Padilla | 4 | 2028-2039 | |
| 59 | Víctor Padilla | 4 | 2017-2020 | |
| 59 | Milutin Panic# | 4 | 2044-2050 | |
| 59 | Coyote Peterson# | 4 | 2045-2049 | |
| 59 | Sidney Petty# | 4 | 2043-2049 | |
| 59 | Carlos Ramos | 4 | 2025-2028 | |
| 59 | Jeff Reynolds | 4 | 2018-2020 | |
| 59 | John Riggleman | 4 | 2026-2040 | |
| 59 | John Rigsby | 4 | 2037-2043 | |
| 59 | Rafael Rivera | 4 | 2026-2040 | |
| 59 | Addie Samson | 4 | 2024-2034 |
