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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Luis Escobar | 134 | 2010-2024 | |
| 2 | Mitch Cain | 113 | 2002-2013 | |
| 3 | Alfredo Contreras# | 112 | 2044-2058 | |
| 3 | Nelson Williams | 112 | 1998-2009 | |
| 5 | Finley Stabb | 107 | 2013-2026 | |
| 6 | Roger Boyd | 104 | 1995-2006 | |
| 7 | Vernon Lewis | 102 | 2016-2028 | |
| 8 | Gill O'Puddin | 100 | 2011-2022 | |
| 8 | Darryl Otterson | 100 | 1997-2005 | |
| 10 | Héctor Méndez | 99 | 2016-2031 | |
| 10 | Jim Pollock# | 99 | 2044-2058 | |
| 12 | Hubert Rogers | 97 | 2015-2025 | |
| 13 | Sean Bergman | 96 | 1995-2008 | |
| 14 | Pedro Tapia | 95 | 2017-2030 | |
| 15 | Tyrell Davis | 93 | 2001-2009 | |
| 15 | Berhane Omondi | 93 | 2038-2050 | |
| 17 | David Hoskins | 91 | 2018-2026 | |
| 17 | Luis Valenzuela | 91 | 2022-2036 | |
| 19 | Ben Pyrmont | 89 | 2036-2047 | |
| 19 | Cliff Sweeny | 89 | 2004-2012 | |
| 21 | Roger Brown | 88 | 2019-2031 | |
| 22 | Tony Canales | 87 | 2023-2040 | |
| 22 | Callum Maybury | 87 | 2035-2044 | |
| 22 | Chico Ramirez | 87 | 1995-2006 | |
| 22 | Rodrigo Rojas | 87 | 1996-2008 | |
| 26 | Domingo Anaya | 86 | 2023-2030 | |
| 26 | Bob Ramírez | 86 | 2037-2049 | |
| 28 | Spike Wagner | 85 | 2033-2048 | |
| 29 | Christopher Robinson | 84 | 2017-2027 | |
| 30 | Lance Carter | 83 | 2037-2049 | |
| 30 | Faustino Flores | 83 | 1998-2005 | |
| 32 | Lee Dalby | 82 | 2018-2030 | |
| 32 | José Olvera | 82 | 2023-2038 | |
| 34 | Derrek Terry | 81 | 2034-2047 | |
| 35 | Andrew Bogan | 80 | 1995-2005 | |
| 35 | Josh Holt | 80 | 2010-2018 | |
| 35 | Justin Lovern | 80 | 1997-2008 | |
| 35 | Adam Spurle | 80 | 1995-2010 | |
| 39 | Albie Lopez | 78 | 1997-2008 | |
| 39 | Arturo Rodríguez | 78 | 2021-2030 | |
| 39 | Timo van Oosterom | 78 | 2027-2041 | |
| 42 | Alfredo Elizarraraz | 77 | 2017-2029 | |
| 42 | Raúl García | 77 | 1998-2004 | |
| 42 | Jon Heard | 77 | 2019-2028 | |
| 42 | Luis Hernández | 77 | 2020-2027 | |
| 42 | Sean Jones | 77 | 1996-2010 | |
| 42 | Marcos Medina | 77 | 2025-2037 | |
| 48 | Matt Drews | 76 | 1995-2009 | |
| 48 | Juan Gonzáles | 76 | 2006-2016 | |
| 48 | Juan Pagán | 76 | 2027-2037 | |
| 51 | Gerardo Arroyo | 75 | 2009-2015 | |
| 51 | David Fernández | 75 | 2010-2017 | |
| 51 | Cody Lee | 75 | 2029-2037 | |
| 54 | Sherman Clubb | 74 | 1996-2007 | |
| 54 | Todd Jones# | 74 | 2048-2058 | |
| 54 | Tommy Lacey | 74 | 1995-2002 | |
| 54 | Rodger Murkami | 74 | 1995-2006 | |
| 54 | Mark Reardon# | 74 | 2051-2058 | |
| 59 | Alberto Bejinez | 73 | 1997-2005 | |
| 59 | Gaspar Garcia | 73 | 1997-2006 | |
| 61 | Steve Ratzlaff | 72 | 2018-2029 | |
| 61 | Richard Wang | 72 | 1996-2003 | |
| 63 | Javier Bautista | 71 | 2024-2032 | |
| 63 | Adel bin Ibrahim | 71 | 2033-2046 | |
| 63 | José Bray# | 71 | 2048-2058 | |
| 63 | Domingo Campa | 71 | 2025-2032 | |
| 63 | Luis López | 71 | 2013-2027 | |
| 63 | Esteban Madera | 71 | 1995-2006 | |
| 63 | Roberto Martínez | 71 | 2022-2035 | |
| 63 | Nick Mobley | 71 | 2040-2055 | |
| 63 | Jeremy Pompey | 71 | 2000-2010 | |
| 63 | Thomas Rodríguez | 71 | 2037-2053 | |
| 63 | William Smith | 71 | 1998-2007 | |
| 63 | Elvin Willard | 71 | 2010-2017 | |
| 75 | Curt Bandelow | 70 | 2002-2010 | |
| 75 | Dani Díaz | 70 | 2011-2016 | |
| 75 | José García | 70 | 2044-2056 | |
| 75 | Kenny Kelly# | 70 | 2045-2055 | |
| 75 | Claudio Silva | 70 | 2019-2027 | |
| 80 | Stacy Bashir | 69 | 1995-2006 | |
| 80 | Berto Gámez | 69 | 2035-2042 | |
| 80 | Eladio Morales | 69 | 1995-2002 | |
| 80 | Marcos Morales | 69 | 2038-2044 | |
| 80 | Tom Rivers | 69 | 2002-2008 | |
| 85 | Berndt Austerlitz | 68 | 2023-2030 | |
| 85 | Willie Evans | 68 | 2016-2028 | |
| 85 | Santiago Gálvez | 68 | 2014-2030 | |
| 85 | Gary McCabe | 68 | 2004-2012 | |
| 85 | Quentin Mullins | 68 | 2042-2055 | |
| 90 | Richard Dallaire | 67 | 2020-2028 | |
| 90 | Andrew Garrison | 67 | 2021-2027 | |
| 90 | Lodewijk Kluin | 67 | 2023-2033 | |
| 90 | Ghi-cheng Kum | 67 | 2035-2053 | |
| 90 | Sam Lawrence | 67 | 2009-2017 | |
| 90 | Jeff Long | 67 | 2001-2011 | |
| 90 | César Ramos | 67 | 2021-2031 | |
| 90 | Augusto Villarreal | 67 | 2039-2047 | |
| 98 | Jeff Clay | 66 | 2013-2021 | |
| 98 | Juan Crespo | 66 | 2017-2022 | |
| 98 | Rudy Forrest | 66 | 2034-2045 |
