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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Franky Sanicencio* | 18 | 2051-2074 | |
| 2 | Bret Kingman | 17 | 2013-2031 | |
| 3 | Orlando Quiñones | 16 | 2025-2037 | |
| 4 | Ocho Aguilar | 15 | 2053-2065 | |
| 5 | Jeffrey Campbell | 14 | 2027-2044 | |
| 5 | Nathan Fry* | 14 | 2033-2054 | |
| 5 | Ron Isham* | 14 | 1990-1999 | |
| 8 | Eddie Izurieta# | 13 | 2063-2084 | |
| 9 | Mario Ausosa* | 12 | 1998-2017 | |
| 9 | Freddie Jonas* | 12 | 1998-2016 | |
| 11 | Stan Bland | 11 | 2013-2030 | |
| 11 | Luis Ríos | 11 | 1990-2005 | |
| 11 | Luis Tamez | 11 | 2060-2077 | |
| 11 | Dewey Wilson | 11 | 2013-2029 | |
| 15 | Ramón Arroyo | 10 | 2019-2029 | |
| 15 | José Baca | 10 | 2034-2049 | |
| 15 | B.J. Baker# | 10 | 2068-2084 | |
| 15 | Mark Brewster | 10 | 2023-2038 | |
| 15 | Che Cannilo | 10 | 2017-2031 | |
| 15 | Sal Casamonica | 10 | 2053-2064 | |
| 15 | Preston Clendinning | 10 | 2000-2015 | |
| 15 | Alex Ewing | 10 | 2013-2027 | |
| 15 | Vismay Falcon# | 10 | 2069-2084 | |
| 15 | Buck Felter | 10 | 2038-2054 | |
| 15 | Tomás Gómez | 10 | 2046-2060 | |
| 15 | John Hersey | 10 | 2064-2081 | |
| 15 | Jorge Illescas | 10 | 2034-2049 | |
| 15 | Alistair Jones | 10 | 2045-2061 | |
| 15 | Gene Morrow* | 10 | 2026-2042 | |
| 15 | Bill Oates | 10 | 2018-2026 | |
| 15 | Dave Rose | 10 | 1999-2014 | |
| 15 | Orlando Siono | 10 | 2050-2065 | |
| 33 | Norgan Alchops* | 9 | 2032-2047 | |
| 33 | Michael Duncan | 9 | 2035-2050 | |
| 33 | Jamie Fletcher | 9 | 2021-2034 | |
| 33 | Gary Gordon | 9 | 2046-2060 | |
| 33 | Tom Kane* | 9 | 2036-2051 | |
| 33 | Craig Kruppenbacher# | 9 | 2074-2084 | |
| 33 | Cristián López | 9 | 2028-2041 | |
| 33 | Horace McKeaver* | 9 | 2038-2057 | |
| 33 | Greg Muldoon* | 9 | 2020-2036 | |
| 33 | Kazuma Nakao | 9 | 2022-2033 | |
| 33 | Mochihito Ohayashi | 9 | 2026-2039 | |
| 33 | Joe Quarterman* | 9 | 2060-2077 | |
| 33 | Joaquín Sousa | 9 | 2009-2024 | |
| 33 | Fernando Varela | 9 | 2013-2029 | |
| 33 | Will White | 9 | 2019-2037 | |
| 48 | Charlie Anderson* | 8 | 2005-2023 | |
| 48 | Antonio Avellaneda# | 8 | 2068-2084 | |
| 48 | Tristan Brandt* | 8 | 2045-2062 | |
| 48 | Antonio Ceballos | 8 | 2058-2076 | |
| 48 | António Detorres | 8 | 2040-2056 | |
| 48 | Larry Duplessis* | 8 | 2012-2030 | |
| 48 | Leonard Logan | 8 | 2002-2015 | |
| 48 | Micah MacInstalker | 8 | 2042-2059 | |
| 48 | Santiago Ontiveros | 8 | 2066-2084 | |
| 48 | Ricardo Pérez | 8 | 1990-2002 | |
| 48 | Danny Quijano | 8 | 2063-2077 | |
| 48 | Dave Stone | 8 | 2031-2041 | |
| 48 | John Sutton | 8 | 2059-2075 | |
| 48 | Nick Tamulevich# | 8 | 2072-2084 | |
| 48 | Andreas Walters* | 8 | 2036-2053 | |
| 63 | Luis Alfonzo* | 7 | 1990-2006 | |
| 63 | Eli Badtree* | 7 | 2018-2037 | |
| 63 | Marnolki Basteiro* | 7 | 2055-2071 | |
| 63 | Luis Cantú* | 7 | 1990-2011 | |
| 63 | Bobby Day* | 7 | 1990-2008 | |
| 63 | Scott Deal* | 7 | 2037-2057 | |
| 63 | Tom Dobie# | 7 | 2077-2084 | |
| 63 | Charlie Durdle | 7 | 2022-2035 | |
| 63 | Wayne Fish | 7 | 1997-2012 | |
| 63 | Zachary Foulkes | 7 | 2045-2061 | |
| 63 | Honey Geier | 7 | 2068-2082 | |
| 63 | Judd Green | 7 | 2006-2020 | |
| 63 | Carver Hollis | 7 | 2018-2028 | |
| 63 | Shirai Ito | 7 | 2020-2038 | |
| 63 | Kenrich Keith* | 7 | 1996-2015 | |
| 63 | Masatake Kouki | 7 | 2000-2014 | |
| 63 | Joseph Langman* | 7 | 2032-2046 | |
| 63 | Chris Lee | 7 | 2031-2047 | |
| 63 | David Lewis | 7 | 2034-2048 | |
| 63 | Juan Morales | 7 | 2043-2054 | |
| 63 | Andre Olderman | 7 | 2052-2068 | |
| 63 | António Padilla | 7 | 2013-2026 | |
| 63 | Matt Porter* | 7 | 2010-2024 | |
| 63 | Jose Santovenia | 7 | 2012-2023 | |
| 63 | Jarred Seals | 7 | 2055-2068 | |
| 63 | John Sexton* | 7 | 2010-2022 | |
| 63 | Jerrel Spits | 7 | 2054-2071 | |
| 63 | Ismael St. James | 7 | 2033-2047 | |
| 63 | Sorai Suitani | 7 | 2014-2025 | |
| 63 | Zhao-ying Ta | 7 | 2014-2028 | |
| 63 | Will Thomas | 7 | 2013-2026 | |
| 63 | Jason Townsley | 7 | 2029-2046 | |
| 63 | Hayden Turner | 7 | 1990-2000 | |
| 63 | Jeff Wren | 7 | 2031-2047 | |
| 97 | Dan Barker | 6 | 2036-2049 | |
| 97 | Kurt Bozek# | 6 | 2074-2084 | |
| 97 | Gary Burkholder | 6 | 2062-2075 | |
| 97 | Steve Cameron | 6 | 2027-2036 |
