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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Bailey Achurch | 38 | 2031-2035 | |
| 2 | Nicolas Roche | 36 | 2027-2030 | |
| 2 | Bill Tennant | 36 | 2035-2038 | |
| 4 | Felipe Hull# | 32 | 2052-2055 | |
| 5 | León Berroa# | 30 | 2053-2057 | |
| 5 | Alfredo Rodríguez | 30 | 2033-2037 | |
| 7 | Edmund Blackadder | 28 | 2026-2030 | |
| 7 | Tim Day# | 28 | 2054-2058 | |
| 7 | Jaime Delegorsa | 28 | 2052-2055 | |
| 7 | Brian Fixel | 28 | 2023-2025 | |
| 11 | Micheal Smith | 27 | 2038-2043 | |
| 12 | Aaron Covington | 26 | 2055-2057 | |
| 12 | Reid Myers | 26 | 2030-2036 | |
| 12 | Greg O'Day | 26 | 2034-2036 | |
| 12 | Ryan Riley | 26 | 2042-2046 | |
| 12 | Octávio Ríos | 26 | 2020-2022 | |
| 12 | Pat Thompson | 26 | 2020-2022 | |
| 18 | Julian Glenn | 25 | 2050-2052 | |
| 18 | Bill Hernández# | 25 | 2059-2060 | |
| 18 | Will Hoffman | 25 | 2026-2028 | |
| 18 | George Kane | 25 | 2030-2034 | |
| 18 | Hyung-ki Kim | 25 | 2029-2033 | |
| 18 | Blaine Stottlar | 25 | 2027-2028 | |
| 18 | Kidlat Tria | 25 | 2032-2036 | |
| 25 | Francisco Chavarría | 24 | 2052-2055 | |
| 25 | Kenny James | 24 | 2035-2037 | |
| 25 | Barry Mullen | 24 | 2028-2030 | |
| 25 | Bruno Mumford | 24 | 2033-2036 | |
| 25 | Miguel Murillo | 24 | 2048-2050 | |
| 25 | Paul Norton# | 24 | 2054-2057 | |
| 25 | Adrian Robertson | 24 | 2034-2037 | |
| 25 | César Rosado | 24 | 2021-2023 | |
| 25 | Pedro Tavárez | 24 | 2024-2027 | |
| 34 | Héctor Aguilar | 23 | 2026-2028 | |
| 34 | Christiansen Chemnitz | 23 | 2043-2046 | |
| 34 | Júlio Díaz | 23 | 2032-2034 | |
| 34 | Nicolaas Eland | 23 | 2037-2042 | |
| 34 | Gilberto Espinoza# | 23 | 2054-2056 | |
| 34 | Sib Gijbels# | 23 | 2055-2057 | |
| 34 | Ronald Hensball | 23 | 2054-2056 | |
| 34 | Hengkie Iriawan | 23 | 2028-2030 | |
| 34 | Paco Manuel | 23 | 2024-2026 | |
| 34 | António Rodríguez | 23 | 2023-2025 | |
| 34 | Marcus Rollock# | 23 | 2054-2056 | |
| 34 | Geoff Stackhouse | 23 | 2025-2029 | |
| 34 | José Vélez | 23 | 2029-2033 | |
| 47 | Marv Bradford | 22 | 2021-2024 | |
| 47 | Henry Fletcher# | 22 | 2059-2061 | |
| 47 | Alejandro García | 22 | 2026-2030 | |
| 47 | Taylor Geldard | 22 | 2030-2034 | |
| 47 | Jesús Guerra | 22 | 2023-2025 | |
| 47 | Kyle Horton | 22 | 2042-2045 | |
| 47 | Rhys Maskell | 22 | 2031-2032 | |
| 47 | Adam McJannett# | 22 | 2057-2061 | |
| 47 | Phil Miller | 22 | 2021-2025 | |
| 47 | Bernardino Neagle | 22 | 2020-2023 | |
| 47 | Freddy Rosas | 22 | 2054-2057 | |
| 47 | Magnus Scheving | 22 | 2023-2026 | |
| 59 | José Archuletu | 21 | 2055-2058 | |
| 59 | Ed Baker# | 21 | 2058-2061 | |
| 59 | Jesús Garces | 21 | 2026-2028 | |
| 59 | Billy Grange | 21 | 2024-2026 | |
| 59 | Edgardo Gutiérrez | 21 | 2050-2052 | |
| 59 | Nate Jackson | 21 | 2031-2032 | |
| 59 | Myles Jones | 21 | 2047-2050 | |
| 59 | Gerbrand Kodde | 21 | 2053-2056 | |
| 59 | Ernest Morales | 21 | 2052-2055 | |
| 59 | Juan Ordóñez | 21 | 2024-2026 | |
| 59 | Júlio Ramírez# | 21 | 2052-2057 | |
| 59 | Cristo Rodríguez | 21 | 2020-2023 | |
| 59 | John Sackett | 21 | 2050-2053 | |
| 59 | Jeff Schneider | 21 | 2020-2021 | |
| 59 | Cameron Sellers | 21 | 2038-2041 | |
| 59 | Bob Smithley# | 21 | 2058-2060 | |
| 59 | Barry St. John# | 21 | 2057-2059 | |
| 59 | Benjamin Weightman | 21 | 2029-2032 | |
| 77 | Nelson Cuevas | 20 | 2026-2028 | |
| 77 | Stanley Eldrige | 20 | 2025-2027 | |
| 77 | Ricardo Ferreira | 20 | 2030-2034 | |
| 77 | Gabriel Herrera | 20 | 2022-2025 | |
| 77 | Jim Hunter | 20 | 2045-2046 | |
| 77 | Chandler Lester | 20 | 2051-2053 | |
| 77 | Felipe López | 20 | 2040-2046 | |
| 77 | Miguel López# | 20 | 2057-2060 | |
| 77 | Dax Marshall | 20 | 2056-2057 | |
| 77 | Mike McKay | 20 | 2026-2029 | |
| 77 | Nathan Mitchell | 20 | 2051-2053 | |
| 77 | José Molina | 20 | 2023-2026 | |
| 77 | Will Moore | 20 | 2023-2025 | |
| 77 | Alberto Ortíz | 20 | 2034-2036 | |
| 77 | Lincoln Spooner | 20 | 2026-2028 | |
| 77 | Reynaldo Sánchez | 20 | 2020-2023 | |
| 77 | Teo van der Meulen | 20 | 2029-2033 | |
| 77 | Pu-feng Zhou | 20 | 2029-2030 | |
| 95 | Fred Bridges | 19 | 2036-2041 | |
| 95 | Enea Dini | 19 | 2020-2024 | |
| 95 | David Fuentes | 19 | 2034-2038 | |
| 95 | Bartolo Guerra | 19 | 2038-2041 | |
| 95 | Esko Haapakoski# | 19 | 2050-2052 | |
| 95 | Vincent Hubbard | 19 | 2035-2037 |
