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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | José Montoya | 95 | 2039-2054 | |
| 2 | Emílio Pérez | 92 | 2038-2046 | |
| 3 | Juan Vado | 90 | 2039-2050 | |
| 4 | Theophilus Markoullides# | 79 | 2051-2056 | |
| 5 | Jack Sellers | 77 | 1997-2007 | |
| 6 | José Garza | 74 | 1995-2002 | |
| 7 | Ralph Leslie | 69 | 1995-2001 | |
| 8 | Ryan Wilson | 67 | 2037-2043 | |
| 9 | Esteban De La Cruz | 66 | 1996-2007 | |
| 9 | Gilberto García | 66 | 1996-2001 | |
| 11 | Augusto Villarreal | 64 | 2038-2053 | |
| 12 | Leonardo Ramos | 63 | 2047-2054 | |
| 13 | Jorge García | 62 | 2036-2051 | |
| 14 | Alonso Chávez# | 61 | 2046-2054 | |
| 14 | Domingo Otero | 61 | 2035-2044 | |
| 16 | Marc Pierson | 60 | 1999-2007 | |
| 17 | Raúl Arteaga | 59 | 2017-2026 | |
| 18 | Millard Bell | 57 | 1995-2008 | |
| 18 | Jesús Piña | 57 | 2037-2043 | |
| 20 | Michael Carlson | 56 | 2037-2045 | |
| 21 | Ambrose McCoy | 55 | 1996-2002 | |
| 22 | José Martínez | 54 | 2003-2008 | |
| 23 | Aurelio Durán | 52 | 2017-2019 | |
| 23 | Nelson Rivera | 52 | 1996-2001 | |
| 23 | Richard Rodda | 52 | 2048-2053 | |
| 26 | Trent Barrett | 51 | 2048-2053 | |
| 26 | Chris Bradley | 51 | 1995-2003 | |
| 26 | Rafael Vega | 51 | 1995-2003 | |
| 26 | Bob Wood | 51 | 1995-2003 | |
| 30 | Pete Hulett# | 50 | 2055-2058 | |
| 31 | Hamilton Bayless | 49 | 1997-2007 | |
| 31 | Jorge Reynoso | 49 | 1995-2001 | |
| 31 | Kim Rodas | 49 | 1995-1998 | |
| 31 | Juan Sánchez | 49 | 2027-2043 | |
| 31 | Carlos Torres# | 49 | 2047-2053 | |
| 36 | Curtis Bhatia | 48 | 1995-1998 | |
| 36 | Lee Brown | 48 | 1995-2000 | |
| 36 | Ron Cameron | 48 | 2037-2044 | |
| 36 | César Castaneda | 48 | 2043-2047 | |
| 36 | Gabriel Hinton | 48 | 2003-2011 | |
| 36 | Samuel Long | 48 | 2006-2013 | |
| 36 | Ryosei Miyazaki | 48 | 2040-2050 | |
| 36 | Francisco Rojas | 48 | 2040-2045 | |
| 36 | António Téllez | 48 | 2036-2044 | |
| 36 | Eduardo Vázquez | 48 | 2040-2049 | |
| 36 | Elvin Willard | 48 | 2007-2010 | |
| 47 | Steve Griffin | 47 | 1995-2007 | |
| 47 | Danny Harrell | 47 | 2002-2007 | |
| 47 | António Jiménez | 47 | 2002-2006 | |
| 47 | Eddie Johnson | 47 | 2013-2023 | |
| 47 | Tsukasa Kumagai | 47 | 2042-2048 | |
| 47 | Ian Stroud | 47 | 2011-2013 | |
| 53 | Simón Bautista | 46 | 2034-2049 | |
| 53 | Cameron Bennett | 46 | 1997-2008 | |
| 53 | Carlos Costa | 46 | 2007-2013 | |
| 53 | José Flores | 46 | 2031-2038 | |
| 53 | Héctor Franjul | 46 | 1995-2001 | |
| 53 | Tetsuzan Saito# | 46 | 2044-2051 | |
| 53 | Alfredo Vanali | 46 | 2034-2040 | |
| 60 | Jon Dyer | 45 | 2006-2009 | |
| 60 | Carlos Días | 45 | 2037-2043 | |
| 60 | Roberto Díaz# | 45 | 2046-2050 | |
| 60 | C.J. Ischade | 45 | 2036-2050 | |
| 60 | John King | 45 | 2013-2017 | |
| 60 | Vicente Romero# | 45 | 2054-2058 | |
| 60 | Okba Shaabani | 45 | 2036-2041 | |
| 60 | Terry White | 45 | 2027-2033 | |
| 68 | José Cueto# | 44 | 2050-2055 | |
| 68 | Tom Davies | 44 | 1998-2009 | |
| 68 | Juan Jose Morán | 44 | 2040-2047 | |
| 68 | Jov Oizerman | 44 | 2045-2052 | |
| 68 | Leo Owen | 44 | 2039-2045 | |
| 68 | Willie Peters | 44 | 2016-2023 | |
| 68 | Terry Utting | 44 | 2014-2023 | |
| 75 | Brian Craft | 43 | 2020-2025 | |
| 75 | Eduardo Flores | 43 | 2017-2025 | |
| 75 | Pat Hughes | 43 | 1995-2001 | |
| 75 | Rob Kennedy | 43 | 2001-2003 | |
| 75 | Raúl Portillo | 43 | 2038-2043 | |
| 75 | António Rivera | 43 | 2025-2029 | |
| 75 | Carlos Zalvidea | 43 | 2000-2003 | |
| 82 | Joe Adams | 42 | 2042-2045 | |
| 82 | Juan Rodríguez | 42 | 2044-2052 | |
| 82 | Pedro Sánchez | 42 | 1995-2001 | |
| 82 | Jesus Torrealba | 42 | 1995-2000 | |
| 82 | Jason Tyler | 42 | 2030-2034 | |
| 87 | Joe Anstey | 41 | 2020-2023 | |
| 87 | Richard Cleveland | 41 | 1995-2001 | |
| 87 | Javier Cruz# | 41 | 2056-2058 | |
| 87 | Jurrie de Jongh | 41 | 2007-2010 | |
| 87 | Vicente Freitas | 41 | 2034-2037 | |
| 87 | Joseph Heywood | 41 | 1995-1999 | |
| 87 | Roy Nealy# | 41 | 2053-2055 | |
| 87 | Jesús Ramírez | 41 | 2005-2013 | |
| 87 | Bango Vadabonceour Jr. | 41 | 1999-2011 | |
| 87 | Logan Williams# | 41 | 2052-2057 | |
| 97 | Miguel Aguirre | 40 | 2020-2025 | |
| 97 | Phil Browne | 40 | 2015-2026 | |
| 97 | Raúl Castro | 40 | 2038-2044 | |
| 97 | Vicente Cedeño | 40 | 2019-2026 |
