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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Michael Calhoun | 78 | 2044-2049 | |
| 2 | Toby Adams | 77 | 2034-2047 | |
| 3 | Michael Dana | 64 | 2010-2017 | |
| 4 | Luis Leyva | 62 | 2013-2019 | |
| 5 | John Campbell | 57 | 2026-2035 | |
| 6 | Brady Walker | 56 | 2036-2050 | |
| 7 | Enzo Echevería# | 55 | 2044-2051 | |
| 7 | Jeffrey Gómez | 55 | 2029-2040 | |
| 9 | António López# | 53 | 2047-2051 | |
| 10 | Robert Collard | 52 | 2029-2047 | |
| 11 | Jesús González# | 51 | 2045-2051 | |
| 12 | Mauro Puñal | 47 | 2010-2020 | |
| 12 | Wynn Thompson | 47 | 2019-2029 | |
| 14 | Jorge Garza# | 46 | 2047-2051 | |
| 15 | Júlio Caraballo | 44 | 2030-2034 | |
| 15 | Ira Franklin | 44 | 2034-2041 | |
| 17 | Will Calderón# | 43 | 2046-2051 | |
| 18 | Roberto Feliciano# | 42 | 2045-2050 | |
| 19 | Rafael González# | 41 | 2037-2050 | |
| 20 | Dave Boyer# | 39 | 2043-2051 | |
| 20 | Mario Contreras# | 39 | 2037-2051 | |
| 20 | Brian Hankins | 39 | 2033-2039 | |
| 20 | Robby Miller | 39 | 2014-2022 | |
| 20 | Ricardo Padilla# | 39 | 2045-2051 | |
| 25 | Rob Johnson | 38 | 2019-2025 | |
| 26 | Nick Coomer | 37 | 2033-2046 | |
| 26 | António Pacheco | 37 | 2028-2039 | |
| 26 | Terry Reed | 37 | 2037-2039 | |
| 29 | Glenn Barker Jr. | 36 | 2029-2039 | |
| 29 | Chad Letchworth | 36 | 2011-2014 | |
| 29 | Mitsuhide Suzuki | 36 | 2030-2044 | |
| 32 | Fernando Díaz# | 35 | 2048-2051 | |
| 32 | Ron Fisher# | 35 | 2047-2051 | |
| 32 | Olivier Martel | 35 | 2030-2044 | |
| 32 | Brandon Ramos# | 35 | 2045-2051 | |
| 36 | Jarred Benson | 34 | 2038-2043 | |
| 36 | Lester Pitts | 34 | 2029-2037 | |
| 38 | Dave Barnes | 33 | 2032-2036 | |
| 38 | Olezka Elizarov | 33 | 2032-2044 | |
| 38 | Francisco Escobedo# | 33 | 2046-2051 | |
| 38 | Jorge Gómez | 33 | 2034-2040 | |
| 38 | Cade Hicks | 33 | 2028-2036 | |
| 38 | Randolph Hutchison | 33 | 2017-2019 | |
| 38 | Frank Martinez | 33 | 2010-2014 | |
| 38 | Bubba McCall# | 33 | 2046-2051 | |
| 38 | Ricardo Medina# | 33 | 2045-2051 | |
| 38 | Jim Miller | 33 | 2032-2034 | |
| 38 | Cipriano Pérez | 33 | 2034-2046 | |
| 38 | Bill Tucker | 33 | 2028-2033 | |
| 50 | Jason Allen# | 32 | 2046-2051 | |
| 50 | José Arrojo | 32 | 2024-2037 | |
| 50 | Javier Córdova | 32 | 2035-2045 | |
| 50 | Matt Miller | 32 | 2013-2016 | |
| 50 | Roberto Romano | 32 | 2034-2039 | |
| 50 | Takanori Watanabe | 32 | 2014-2018 | |
| 56 | Pancho Hernández# | 31 | 2049-2051 | |
| 56 | Mark King | 31 | 2036-2041 | |
| 56 | Aaron Peterson# | 31 | 2043-2051 | |
| 56 | Jason Ryan | 31 | 2027-2032 | |
| 60 | Paul Bechenoe | 30 | 2028-2037 | |
| 60 | Bill Davis | 30 | 2030-2037 | |
| 60 | Bernardo De Jesús# | 30 | 2046-2051 | |
| 60 | Billy Gilbert# | 30 | 2048-2051 | |
| 60 | Patrick Leighton | 30 | 2021-2023 | |
| 60 | Francisco Machado | 30 | 2033-2035 | |
| 60 | James Martin | 30 | 2038-2046 | |
| 60 | Horiuchi Morishita | 30 | 2011-2014 | |
| 60 | Clay Patterson | 30 | 2038-2045 | |
| 69 | Tashfin Amara | 29 | 2014-2020 | |
| 69 | Manny Flores | 29 | 2029-2038 | |
| 69 | Rodrigo Hernández | 29 | 2036-2037 | |
| 69 | Josh Lord | 29 | 2016-2017 | |
| 69 | Wendell MacNeill# | 29 | 2039-2051 | |
| 69 | Mauro Olivas | 29 | 2013-2016 | |
| 69 | Paul Parker | 29 | 2032-2049 | |
| 69 | Jack Robinson | 29 | 2030-2039 | |
| 69 | Shih-k'ai Su-Tu | 29 | 2033-2040 | |
| 78 | Sozui Daikawa# | 28 | 2043-2051 | |
| 78 | José Fernández | 28 | 2026-2032 | |
| 78 | Sergio García | 28 | 2038-2045 | |
| 78 | Clint Henderson# | 28 | 2048-2051 | |
| 78 | Jim Moon | 28 | 2012-2017 | |
| 78 | Ernest Nelson | 28 | 2017-2034 | |
| 78 | Felipe Pérez | 28 | 2032-2034 | |
| 78 | Sergio Rivera# | 28 | 2047-2051 | |
| 78 | Jorian van Ankeren | 28 | 2040-2047 | |
| 87 | Derek Howard | 27 | 2038-2041 | |
| 87 | Doug Roberts | 27 | 2012-2014 | |
| 87 | Craig Robinson | 27 | 2041-2043 | |
| 87 | Iván Sandoval# | 27 | 2043-2045 | |
| 87 | Juan Villarreal | 27 | 2034-2046 | |
| 87 | Pete Walker | 27 | 2031-2034 | |
| 87 | Elvis Warren | 27 | 2028-2032 | |
| 94 | Roberto Alvardo | 26 | 2043-2046 | |
| 94 | Chris Beaumond# | 26 | 2049-2051 | |
| 94 | Iván Costa | 26 | 2012-2014 | |
| 94 | Jaime Hernández | 26 | 2043-2047 | |
| 94 | Josh Hobbs# | 26 | 2049-2051 | |
| 94 | Mike McAindra | 26 | 2012-2016 | |
| 94 | Pedro Moreno | 26 | 2024-2030 |
