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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Rod O'Colgan* | 33 | 2014-2035 | |
| 2 | Jon Givens* | 21 | 2013-2026 | |
| 3 | Norman Cornell* | 20 | 2037-2050 | |
| 4 | Ron Carmichael | 16 | 2025-2047 | |
| 4 | Jorge Ramírez* | 16 | 2036-2053 | |
| 4 | Tony Young* | 16 | 2016-2031 | |
| 7 | Pat Bowles* | 15 | 2021-2041 | |
| 7 | Jesús Cruz* | 15 | 2038-2052 | |
| 7 | Héctor Gonzáles | 15 | 2036-2051 | |
| 7 | António Mata | 15 | 2049-2060 | |
| 11 | Sean Fontenot | 14 | 2029-2041 | |
| 11 | Juan Guevara | 14 | 2035-2051 | |
| 11 | Jeff Todd# | 14 | 2053-2065 | |
| 14 | Juan Ramos | 13 | 2037-2052 | |
| 14 | Jorge Reyes | 13 | 2039-2057 | |
| 14 | José Silva* | 13 | 2030-2048 | |
| 17 | Cris Colón | 12 | 2041-2056 | |
| 17 | Sam Johnson# | 12 | 2052-2065 | |
| 17 | Norberto León* | 12 | 2013-2026 | |
| 17 | Leonardo Mendoza* | 12 | 2038-2052 | |
| 17 | Jesús Ortega | 12 | 2034-2048 | |
| 22 | Ken Glass* | 11 | 2017-2032 | |
| 22 | Chris Johnston | 11 | 2015-2034 | |
| 22 | Ron McCormick | 11 | 2048-2057 | |
| 22 | Mike Powell | 11 | 2024-2034 | |
| 22 | Richello Quiogue | 11 | 2049-2060 | |
| 22 | Jerry Sánchez | 11 | 2024-2037 | |
| 22 | Tony Trejo# | 11 | 2060-2065 | |
| 29 | Raul Arvelos# | 10 | 2054-2065 | |
| 29 | Greg Kelley# | 10 | 2057-2065 | |
| 29 | Curt Peterson | 10 | 2030-2046 | |
| 29 | Odwin Reijssen | 10 | 2043-2060 | |
| 29 | Kevin Reynolds | 10 | 2013-2028 | |
| 29 | Dan Sampson# | 10 | 2056-2065 | |
| 29 | Ron Taylor* | 10 | 2013-2037 | |
| 29 | Steve Vincent* | 10 | 2023-2038 | |
| 37 | Juan Castillo* | 9 | 2015-2034 | |
| 37 | Brad Chandler | 9 | 2052-2060 | |
| 37 | Steve Gamble | 9 | 2037-2051 | |
| 37 | Ron Gregory | 9 | 2017-2032 | |
| 37 | Luis Gómez# | 9 | 2053-2065 | |
| 37 | Rob Kirby | 9 | 2014-2025 | |
| 37 | Steve Lloyd | 9 | 2013-2024 | |
| 37 | José Rosário | 9 | 2024-2035 | |
| 45 | Lou Best | 8 | 2043-2060 | |
| 45 | Bobby Burnett | 8 | 2018-2035 | |
| 45 | Ed Cobb# | 8 | 2058-2065 | |
| 45 | Ben Jones | 8 | 2023-2036 | |
| 45 | Ron Martin | 8 | 2013-2028 | |
| 45 | Cristo Mota* | 8 | 2045-2059 | |
| 45 | Katsuyoshi Nakamura* | 8 | 2017-2032 | |
| 45 | Isacco Pomardi# | 8 | 2052-2065 | |
| 45 | Orlando Pérez | 8 | 2023-2042 | |
| 45 | Jorge Rivera | 8 | 2029-2037 | |
| 45 | Jorge Sepúlveda* | 8 | 2013-2023 | |
| 45 | Kel Walden | 8 | 2024-2037 | |
| 45 | Mike Woodard# | 8 | 2049-2061 | |
| 45 | Bobby Young | 8 | 2038-2048 | |
| 59 | Bob Allen | 7 | 2022-2033 | |
| 59 | Jake Ashley | 7 | 2032-2043 | |
| 59 | Rubén Ferreira* | 7 | 2023-2039 | |
| 59 | Sean Garnett | 7 | 2041-2056 | |
| 59 | Ned Haas* | 7 | 2013-2026 | |
| 59 | Matt Hager# | 7 | 2062-2065 | |
| 59 | Johnny Henry | 7 | 2013-2026 | |
| 59 | Cipriano Hernández | 7 | 2014-2027 | |
| 59 | Tommy Jacobson | 7 | 2022-2038 | |
| 59 | Shawn Jenkins | 7 | 2047-2059 | |
| 59 | Gabe Long# | 7 | 2051-2064 | |
| 59 | Jorge Mendoza | 7 | 2051-2063 | |
| 59 | Jeff Mitchell | 7 | 2046-2059 | |
| 59 | Jeff Parker | 7 | 2056-2064 | |
| 59 | Juan Santiago | 7 | 2046-2055 | |
| 59 | Jon Simms* | 7 | 2019-2036 | |
| 59 | Yu-zeng Sung | 7 | 2032-2044 | |
| 59 | Jim Talley | 7 | 2023-2041 | |
| 59 | Christiaan van Meel | 7 | 2042-2057 | |
| 78 | Dennis Ackerstrom# | 6 | 2060-2065 | |
| 78 | Judite Aldeinha# | 6 | 2058-2065 | |
| 78 | Phil Baker* | 6 | 2019-2037 | |
| 78 | Dana Bolen | 6 | 2024-2034 | |
| 78 | Stan Butler | 6 | 2048-2060 | |
| 78 | Alan Carpenter | 6 | 2046-2062 | |
| 78 | Bob Cook | 6 | 2016-2028 | |
| 78 | Mark Davidson# | 6 | 2054-2065 | |
| 78 | Bobby Dodson | 6 | 2021-2037 | |
| 78 | Derrek English | 6 | 2039-2050 | |
| 78 | José Esquivel | 6 | 2039-2052 | |
| 78 | Paço Estaa# | 6 | 2052-2065 | |
| 78 | Jim Fish | 6 | 2024-2040 | |
| 78 | José González | 6 | 2045-2062 | |
| 78 | Joe Haines | 6 | 2013-2020 | |
| 78 | Dave Haug* | 6 | 2017-2036 | |
| 78 | Teimua Kirisitopa | 6 | 2040-2050 | |
| 78 | Tim Lees | 6 | 2024-2038 | |
| 78 | Jeff Locke | 6 | 2045-2058 | |
| 78 | Jorge Luna | 6 | 2022-2039 | |
| 78 | Jorge Maldonado# | 6 | 2058-2065 | |
| 78 | Florante Marrald | 6 | 2014-2032 | |
| 78 | Willie McCann | 6 | 2013-2027 |
