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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 | Jaime Delegorsa# | 28 | 2052-2055 | |
| 7 | Brian Fixel | 28 | 2023-2025 | |
| 10 | Micheal Smith | 27 | 2038-2043 | |
| 11 | Aaron Covington# | 26 | 2055-2057 | |
| 11 | Reid Myers | 26 | 2030-2036 | |
| 11 | Greg O'Day | 26 | 2034-2036 | |
| 11 | Ryan Riley | 26 | 2042-2046 | |
| 11 | Octávio Ríos | 26 | 2020-2022 | |
| 11 | Pat Thompson | 26 | 2020-2022 | |
| 17 | Tim Day# | 25 | 2054-2057 | |
| 17 | Julian Glenn# | 25 | 2050-2052 | |
| 17 | Will Hoffman | 25 | 2026-2028 | |
| 17 | George Kane | 25 | 2030-2034 | |
| 17 | Hyung-ki Kim | 25 | 2029-2033 | |
| 17 | Blaine Stottlar | 25 | 2027-2028 | |
| 17 | Kidlat Tria | 25 | 2032-2036 | |
| 24 | Francisco Chavarría# | 24 | 2052-2055 | |
| 24 | Kenny James | 24 | 2035-2037 | |
| 24 | Barry Mullen | 24 | 2028-2030 | |
| 24 | Bruno Mumford | 24 | 2033-2036 | |
| 24 | Miguel Murillo | 24 | 2048-2050 | |
| 24 | Paul Norton# | 24 | 2054-2057 | |
| 24 | Adrian Robertson | 24 | 2034-2037 | |
| 24 | César Rosado | 24 | 2021-2023 | |
| 24 | Pedro Tavárez | 24 | 2024-2027 | |
| 33 | Héctor Aguilar | 23 | 2026-2028 | |
| 33 | Christiansen Chemnitz | 23 | 2043-2046 | |
| 33 | Júlio Díaz | 23 | 2032-2034 | |
| 33 | Nicolaas Eland | 23 | 2037-2042 | |
| 33 | Gilberto Espinoza# | 23 | 2054-2056 | |
| 33 | Sib Gijbels# | 23 | 2055-2057 | |
| 33 | Ronald Hensball# | 23 | 2054-2056 | |
| 33 | Hengkie Iriawan | 23 | 2028-2030 | |
| 33 | Paco Manuel | 23 | 2024-2026 | |
| 33 | António Rodríguez | 23 | 2023-2025 | |
| 33 | Marcus Rollock# | 23 | 2054-2056 | |
| 33 | Geoff Stackhouse | 23 | 2025-2029 | |
| 33 | José Vélez | 23 | 2029-2033 | |
| 46 | Marv Bradford | 22 | 2021-2024 | |
| 46 | Alejandro García | 22 | 2026-2030 | |
| 46 | Taylor Geldard | 22 | 2030-2034 | |
| 46 | Jesús Guerra | 22 | 2023-2025 | |
| 46 | Kyle Horton | 22 | 2042-2045 | |
| 46 | Rhys Maskell | 22 | 2031-2032 | |
| 46 | Phil Miller | 22 | 2021-2025 | |
| 46 | Bernardino Neagle | 22 | 2020-2023 | |
| 46 | Freddy Rosas# | 22 | 2054-2057 | |
| 46 | Magnus Scheving | 22 | 2023-2026 | |
| 56 | Jesús Garces | 21 | 2026-2028 | |
| 56 | Billy Grange | 21 | 2024-2026 | |
| 56 | Edgardo Gutiérrez# | 21 | 2050-2052 | |
| 56 | Nate Jackson | 21 | 2031-2032 | |
| 56 | Myles Jones | 21 | 2047-2050 | |
| 56 | Gerbrand Kodde# | 21 | 2053-2056 | |
| 56 | Ernest Morales# | 21 | 2052-2055 | |
| 56 | Juan Ordóñez | 21 | 2024-2026 | |
| 56 | Júlio Ramírez# | 21 | 2052-2057 | |
| 56 | Cristo Rodríguez | 21 | 2020-2023 | |
| 56 | John Sackett | 21 | 2050-2053 | |
| 56 | Jeff Schneider | 21 | 2020-2021 | |
| 56 | Cameron Sellers | 21 | 2038-2041 | |
| 56 | Benjamin Weightman | 21 | 2029-2032 | |
| 70 | Nelson Cuevas | 20 | 2026-2028 | |
| 70 | Stanley Eldrige | 20 | 2025-2027 | |
| 70 | Ricardo Ferreira | 20 | 2030-2034 | |
| 70 | Gabriel Herrera | 20 | 2022-2025 | |
| 70 | Jim Hunter# | 20 | 2045-2046 | |
| 70 | Chandler Lester | 20 | 2051-2053 | |
| 70 | Felipe López# | 20 | 2040-2046 | |
| 70 | Dax Marshall# | 20 | 2056-2057 | |
| 70 | Mike McKay | 20 | 2026-2029 | |
| 70 | Nathan Mitchell | 20 | 2051-2053 | |
| 70 | José Molina | 20 | 2023-2026 | |
| 70 | Will Moore | 20 | 2023-2025 | |
| 70 | Alberto Ortíz | 20 | 2034-2036 | |
| 70 | Lincoln Spooner | 20 | 2026-2028 | |
| 70 | Reynaldo Sánchez | 20 | 2020-2023 | |
| 70 | Teo van der Meulen | 20 | 2029-2033 | |
| 70 | Pu-feng Zhou | 20 | 2029-2030 | |
| 87 | Fred Bridges | 19 | 2036-2041 | |
| 87 | Enea Dini | 19 | 2020-2024 | |
| 87 | David Fuentes | 19 | 2034-2038 | |
| 87 | Bartolo Guerra | 19 | 2038-2041 | |
| 87 | Esko Haapakoski# | 19 | 2050-2052 | |
| 87 | Vincent Hubbard | 19 | 2035-2037 | |
| 87 | Pat Inman | 19 | 2034-2036 | |
| 87 | Hong-bo Liu# | 19 | 2049-2051 | |
| 87 | Dave Mason | 19 | 2020-2022 | |
| 87 | Kagetoki Matsubara | 19 | 2027-2028 | |
| 87 | Jeff McBride | 19 | 2034-2037 | |
| 87 | Chris Morris# | 19 | 2053-2054 | |
| 87 | Alberto Ortíz | 19 | 2029-2034 | |
| 87 | Lúcio Padilla | 19 | 2051-2052 |
