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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Finn Poole | 27 | 2036-2039 | |
| 2 | Pánfilo De La Cruz | 26 | 2030-2034 | |
| 3 | Beau Soria | 25 | 2029-2033 | |
| 4 | Briggs Bolin# | 23 | 2040-2043 | |
| 4 | Nick Forquer | 23 | 2040-2043 | |
| 4 | Cody Middleton | 23 | 2031-2033 | |
| 7 | Rowan Childers# | 22 | 2043-2046 | |
| 8 | Brian Daniels# | 21 | 2043-2046 | |
| 8 | Ashley Gauthier | 21 | 2030-2033 | |
| 10 | Dawson Deese# | 20 | 2042-2045 | |
| 10 | Vince Ulrich | 20 | 2007-2010 | |
| 12 | Matt Blanton | 19 | 2043-2046 | |
| 12 | V.J. Bounds# | 19 | 2035-2037 | |
| 12 | Victor Gomez | 19 | 2026-2027 | |
| 15 | Orlando Burgos | 18 | 2016-2018 | |
| 15 | Volaré Falcon | 18 | 2034-2036 | |
| 15 | Theodore Hernandez | 18 | 2030-2032 | |
| 15 | Dana Littmann | 18 | 2036-2039 | |
| 15 | Mike Lopez | 18 | 2025-2026 | |
| 15 | Dan Paterson | 18 | 2033-2035 | |
| 15 | Jameson Roberts# | 18 | 2044-2047 | |
| 15 | Roberto Silva | 18 | 2026-2028 | |
| 23 | Jose Aguirre | 17 | 2004-2006 | |
| 23 | Cameron Beltrami | 17 | 2032-2036 | |
| 23 | Emmet Burton# | 17 | 2043-2047 | |
| 23 | Aaron Evans | 17 | 2026-2027 | |
| 23 | Antonio Viruet | 17 | 2026-2028 | |
| 23 | John Webb# | 17 | 2040-2042 | |
| 29 | Eric Bell | 16 | 2038-2041 | |
| 29 | Oldemar Braud# | 16 | 2039-2043 | |
| 29 | Trevor Bridges | 16 | 2020-2021 | |
| 29 | Wilson Cantu | 16 | 2025-2028 | |
| 29 | Josh Carson | 16 | 2020-2022 | |
| 29 | Allen Daniels | 16 | 2004-2006 | |
| 29 | Keith Elliott | 16 | 2038-2041 | |
| 29 | Alden Fuentes | 16 | 2028-2030 | |
| 29 | Vern Harlow# | 16 | 2045-2048 | |
| 29 | Rush Harvey | 16 | 2034-2036 | |
| 29 | Dave Herrera | 16 | 2007-2009 | |
| 29 | Corbin Holmes# | 16 | 2049-2050 | |
| 29 | Zach Holst# | 16 | 2045-2047 | |
| 29 | Evan Kingsley# | 16 | 2045-2047 | |
| 29 | Jordan Manzanares# | 16 | 2042-2045 | |
| 29 | Nate Martin | 16 | 2008-2010 | |
| 29 | Iker Parra# | 16 | 2048-2050 | |
| 29 | Muhamet Peco | 16 | 2004-2005 | |
| 29 | Chris Reynolds | 16 | 2029-2031 | |
| 29 | Reyes Rivera | 16 | 2027-2030 | |
| 29 | B.J. Whitmore | 16 | 2038-2041 | |
| 29 | Su'ud Youssef | 16 | 2020-2022 | |
| 51 | Octavio Aleman | 15 | 2028-2030 | |
| 51 | Jools Anthony# | 15 | 2049-2050 | |
| 51 | Luis Badillo | 15 | 2027-2029 | |
| 51 | Stewart Banks# | 15 | 2041-2043 | |
| 51 | Luke Barry# | 15 | 2035-2036 | |
| 51 | Eliseo Birkmaier | 15 | 2041-2043 | |
| 51 | Dontari Brooks# | 15 | 2038-2041 | |
| 51 | Júlio Cabrera | 15 | 2029-2031 | |
| 51 | Tolunay Cobanoglu | 15 | 2008-2010 | |
| 51 | De'von Dillard# | 15 | 2040-2042 | |
| 51 | Sol Echevarria# | 15 | 2044-2047 | |
| 51 | Mitch Erickson | 15 | 2035-2038 | |
| 51 | Albertin Estrada | 15 | 2032-2033 | |
| 51 | Pablo Hernandez | 15 | 2010-2014 | |
| 51 | Lyle Kelly | 15 | 2030-2034 | |
| 51 | Dale Kimbrough | 15 | 2032-2034 | |
| 51 | Silas Kringen# | 15 | 2048-2050 | |
| 51 | Elias Mendoza | 15 | 2008-2009 | |
| 51 | Napoleon Palmer# | 15 | 2036-2038 | |
| 51 | Alex Patino | 15 | 2021-2023 | |
| 51 | Chris Pimentel | 15 | 2023-2025 | |
| 51 | Zachary Ribble | 15 | 2025-2027 | |
| 51 | Luís Rosa | 15 | 2034-2036 | |
| 51 | Wagner Saville | 15 | 2040-2042 | |
| 51 | Mark Solly# | 15 | 2043-2046 | |
| 51 | J.R. Thornock# | 15 | 2046-2048 | |
| 51 | Tony Velasquez | 15 | 2020-2022 | |
| 51 | Theodore Vincent# | 15 | 2047-2049 | |
| 51 | Michael Wilson-Brown# | 15 | 2037-2039 | |
| 80 | Jeremy Alles | 14 | 2011-2012 | |
| 80 | Frank Ayala | 14 | 2025-2027 | |
| 80 | Mark Bailey | 14 | 2029-2032 | |
| 80 | Ismael Cardoso | 14 | 2010-2011 | |
| 80 | Jason Collier | 14 | 2015-2017 | |
| 80 | R.J. Coulter# | 14 | 2046-2050 | |
| 80 | Zhang-sung Dan | 14 | 2004-2007 | |
| 80 | Gabriel de Jesus | 14 | 2010-2011 | |
| 80 | Jose Flores | 14 | 2026-2028 | |
| 80 | David Garcia | 14 | 2016-2018 | |
| 80 | Roberto Guzman | 14 | 2017-2020 | |
| 80 | Ron Harris | 14 | 2009-2012 | |
| 80 | Felix Heredia# | 14 | 2044-2048 | |
| 80 | Andy Hernandez | 14 | 2007-2009 | |
| 80 | Alfredo Hoyos | 14 | 2007-2008 | |
| 80 | Matt Juarez | 14 | 2042-2045 | |
| 80 | Chris Lisenby | 14 | 2027-2029 | |
| 80 | Josbiel Palomar | 14 | 2037-2039 | |
| 80 | Christian Perino# | 14 | 2042-2044 | |
| 80 | Aidan Phillips# | 14 | 2044-2047 | |
| 80 | Raúl Quezada | 14 | 2031-2034 |
