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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Terry Ramsey | 69 | 2014-2019 | |
| 2 | Vicente Magana# | 54 | 2045-2050 | |
| 3 | Wynn Thompson | 53 | 2018-2036 | |
| 4 | David Núñez | 46 | 2023-2025 | |
| 5 | Edmund Wise | 39 | 2040-2050 | |
| 6 | Chris Spencer | 38 | 2013-2017 | |
| 7 | Peter Carter | 37 | 2020-2026 | |
| 8 | Luis López# | 35 | 2046-2051 | |
| 8 | Floyd Rivera | 35 | 2042-2045 | |
| 8 | José Zúñiga | 35 | 2016-2019 | |
| 11 | Gene Sanders | 34 | 2014-2017 | |
| 12 | Gerardo Álvarez | 33 | 2018-2020 | |
| 12 | Miguel Fernández# | 33 | 2046-2050 | |
| 12 | Kensaku Sato | 33 | 2024-2035 | |
| 15 | Sean Gilmore | 32 | 2040-2051 | |
| 15 | Pedro Reyes | 32 | 2043-2048 | |
| 15 | Ricardo Trejo | 32 | 2025-2038 | |
| 18 | Rory Taverner | 31 | 2021-2024 | |
| 19 | Will Keller# | 30 | 2048-2051 | |
| 19 | Mark McDaniel | 30 | 2022-2027 | |
| 21 | Elvis Dobson | 29 | 2032-2035 | |
| 21 | George Ellis | 29 | 2023-2036 | |
| 21 | Jorge Gonzáles# | 29 | 2045-2050 | |
| 21 | Jud Horn | 29 | 2021-2031 | |
| 21 | David Moreno# | 29 | 2049-2051 | |
| 26 | Erik Alexander# | 28 | 2047-2050 | |
| 26 | Duane Carter | 28 | 2019-2026 | |
| 26 | Miguel Angel Enríquez# | 28 | 2039-2041 | |
| 29 | Brad Chapman | 27 | 2011-2013 | |
| 29 | Travis Coleman# | 27 | 2047-2049 | |
| 29 | Alberto Gómez# | 27 | 2039-2045 | |
| 29 | Oriol Jaramillo | 27 | 2012-2013 | |
| 29 | Alex MacAdam | 27 | 2033-2036 | |
| 29 | Jean-François Massicotte | 27 | 2031-2033 | |
| 29 | Everett Rijo# | 27 | 2047-2051 | |
| 29 | Jack Sandford | 27 | 2031-2034 | |
| 29 | Dale Warren | 27 | 2018-2019 | |
| 38 | Travis Boyle | 26 | 2036-2038 | |
| 38 | Max Frankcombe# | 26 | 2047-2051 | |
| 38 | Matt Lewis | 26 | 2020-2024 | |
| 38 | Brett O'Halloran | 26 | 2024-2027 | |
| 38 | Marc Pettifer | 26 | 2026-2037 | |
| 38 | Eugene Woods | 26 | 2031-2033 | |
| 44 | Adam Clark | 25 | 2020-2021 | |
| 44 | Mike Conroy | 25 | 2022-2023 | |
| 44 | Richard Davis | 25 | 2024-2026 | |
| 44 | Fernão Ega# | 25 | 2049-2051 | |
| 44 | Kung Kan# | 25 | 2046-2050 | |
| 44 | Bert Molina | 25 | 2045-2049 | |
| 44 | Wilbert Sutton | 25 | 2030-2031 | |
| 44 | Dave Willis | 25 | 2036-2037 | |
| 52 | Arnie Graham | 24 | 2029-2030 | |
| 52 | Derek Howard | 24 | 2036-2037 | |
| 52 | Will Johnson | 24 | 2014-2016 | |
| 52 | Ronald Krieger | 24 | 2014-2017 | |
| 52 | Jim McDonald# | 24 | 2047-2049 | |
| 52 | Carlos Montaño | 24 | 2038-2039 | |
| 52 | Raúl Morán | 24 | 2037-2038 | |
| 52 | Joe Pearson | 24 | 2030-2035 | |
| 52 | Pedro Puerla | 24 | 2035-2037 | |
| 52 | Tyrone Wellburn | 24 | 2035-2037 | |
| 62 | Paul Bechenoe | 23 | 2026-2028 | |
| 62 | Conan Boxer | 23 | 2034-2037 | |
| 62 | António Icaza# | 23 | 2048-2051 | |
| 62 | Thomas Marcoux | 23 | 2022-2024 | |
| 62 | Earl Miller | 23 | 2032-2036 | |
| 62 | Quan Moy# | 23 | 2046-2051 | |
| 62 | Luigi Pedane# | 23 | 2046-2049 | |
| 62 | Chris Shield# | 23 | 2042-2051 | |
| 62 | Brian Sweet | 23 | 2029-2032 | |
| 62 | Toby Valentín# | 23 | 2049-2050 | |
| 62 | Jason Wilkerson | 23 | 2016-2018 | |
| 73 | Dave Barnes | 22 | 2028-2031 | |
| 73 | Carl Bean | 22 | 2043-2045 | |
| 73 | Lorenzo Castaneda | 22 | 2038-2039 | |
| 73 | Rick Dooley | 22 | 2026-2032 | |
| 73 | Juan Flores | 22 | 2021-2022 | |
| 73 | Lee Lynch | 22 | 2016-2018 | |
| 73 | Dave Novak | 22 | 2016-2019 | |
| 73 | Doug O'Halloran | 22 | 2017-2022 | |
| 73 | Luis Osorio# | 22 | 2046-2048 | |
| 73 | José Rodríguez# | 22 | 2045-2046 | |
| 73 | Alfredo Romero# | 22 | 2049-2051 | |
| 73 | Lorenzo Valdés# | 22 | 2045-2051 | |
| 85 | Steve Donahue# | 21 | 2046-2048 | |
| 85 | Ray Maynard# | 21 | 2041-2051 | |
| 85 | Roy McAuslan | 21 | 2031-2038 | |
| 85 | Andrew Phillips# | 21 | 2049-2051 | |
| 85 | Leonard Terry# | 21 | 2048-2050 | |
| 85 | Artie Wade# | 21 | 2049-2051 | |
| 85 | Bill Wall | 21 | 2029-2030 | |
| 85 | Dudley Yates | 21 | 2033-2035 | |
| 93 | Myles Adams# | 20 | 2049-2051 | |
| 93 | Bret Beatty# | 20 | 2047-2049 | |
| 93 | Nick Coomer | 20 | 2031-2034 | |
| 93 | Olezka Elizarov | 20 | 2032-2042 | |
| 93 | Carlos Gallegos | 20 | 2024-2025 | |
| 93 | Larry Halverson | 20 | 2043-2045 | |
| 93 | Cade Hicks | 20 | 2027-2031 | |
| 93 | Randy Johnson# | 20 | 2050-2051 |
