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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Tom Dunne | 51 | 2008-2011 | |
| 2 | Juan Medina | 50 | 2029-2033 | |
| 3 | Tom Petrie | 46 | 2005-2010 | |
| 4 | Jorge Burgos | 42 | 2005-2010 | |
| 4 | Landon Cox | 42 | 2035-2042 | |
| 4 | Umberto Solis | 42 | 2028-2030 | |
| 7 | Isaac de Cler# | 41 | 2048-2050 | |
| 7 | Alex McCants | 41 | 2010-2013 | |
| 9 | Billy Roarty | 39 | 2009-2013 | |
| 9 | Jesus Sena | 39 | 2025-2027 | |
| 11 | Jordan Angel | 38 | 2015-2019 | |
| 11 | Victor Lujan | 38 | 2021-2028 | |
| 11 | Pedro Suarez | 38 | 2012-2014 | |
| 14 | LaTroy Fernandez | 37 | 2035-2038 | |
| 15 | Christofer Elias | 36 | 2033-2036 | |
| 15 | Luis Mendoza | 36 | 2004-2006 | |
| 15 | Nicolás Rey | 36 | 2039-2041 | |
| 15 | Danny Velez | 36 | 2014-2018 | |
| 19 | Marco Cabello | 35 | 2012-2015 | |
| 19 | Rich Henderson# | 35 | 2035-2038 | |
| 19 | Brett Hoffman | 35 | 2024-2026 | |
| 19 | Hoyt Malone | 35 | 2040-2043 | |
| 19 | Sherwin Sandefer | 35 | 2042-2045 | |
| 24 | Steve Aden | 34 | 2026-2028 | |
| 24 | Pat Wheeler | 34 | 2005-2006 | |
| 26 | Jeff Boxell | 33 | 2022-2025 | |
| 26 | Spencer Cartwright | 33 | 2038-2040 | |
| 26 | Luis Ramirez | 33 | 2004-2006 | |
| 29 | Luis Caceres | 32 | 2007-2009 | |
| 29 | Levi Carr# | 32 | 2045-2049 | |
| 29 | Frank Chavez | 32 | 2032-2033 | |
| 29 | Miguel Ferrer | 32 | 2029-2030 | |
| 29 | Jimmy Godwin | 32 | 2004-2007 | |
| 34 | Ernesto Abeyta | 31 | 2004-2006 | |
| 34 | Zak Callahan | 31 | 2038-2040 | |
| 34 | Jake Campbell | 31 | 2029-2032 | |
| 34 | Ricardo Guerrero | 31 | 2028-2030 | |
| 34 | Sergio Leyva | 31 | 2004-2008 | |
| 34 | Armando Perez | 31 | 2029-2032 | |
| 34 | Jim Pipher | 31 | 2004-2006 | |
| 34 | Dave Vazquez | 31 | 2028-2032 | |
| 34 | Homer Weaver | 31 | 2038-2042 | |
| 43 | Ben Albright | 30 | 2004-2008 | |
| 43 | Eddie Burgos | 30 | 2005-2008 | |
| 43 | Rafael Cardeñas | 30 | 2031-2035 | |
| 43 | Ben Ratzloff | 30 | 2039-2041 | |
| 43 | Angel Reyes | 30 | 2011-2014 | |
| 43 | Adrian Toro | 30 | 2033-2035 | |
| 43 | Cole Walker | 30 | 2042-2045 | |
| 50 | Ryan Koester | 29 | 2036-2041 | |
| 50 | Miguel Quito | 29 | 2008-2012 | |
| 50 | Adam Revels# | 29 | 2047-2050 | |
| 50 | Bubba Stancato | 29 | 2004-2006 | |
| 50 | Johnny Weber# | 29 | 2036-2038 | |
| 55 | Steve Angel# | 28 | 2046-2050 | |
| 55 | Ezequiel Avitia | 28 | 2004-2006 | |
| 55 | Oscar Batista | 28 | 2019-2021 | |
| 55 | Andy Benton | 28 | 2021-2023 | |
| 55 | Oldemar Braud# | 28 | 2045-2046 | |
| 55 | Armando Corona | 28 | 2021-2027 | |
| 55 | Jesse Mahan | 28 | 2007-2009 | |
| 55 | Dino Norton | 28 | 2040-2043 | |
| 55 | Frédéric Payano | 28 | 2019-2022 | |
| 55 | Ronaldo Picon | 28 | 2030-2033 | |
| 55 | Chris Pomroy | 28 | 2009-2011 | |
| 55 | Robby Saca | 28 | 2031-2033 | |
| 55 | Cápulet Sandoval | 28 | 2033-2036 | |
| 55 | Chester Tobon | 28 | 2040-2041 | |
| 55 | Willie Ubeda | 28 | 2016-2018 | |
| 55 | Sergio Urrutia | 28 | 2005-2008 | |
| 71 | Mike Arellano | 27 | 2020-2021 | |
| 71 | Hector Botello | 27 | 2027-2029 | |
| 71 | Leuri Castillo# | 27 | 2041-2043 | |
| 71 | Caleb Davis | 27 | 2004-2006 | |
| 71 | Sean Dimson | 27 | 2045-2047 | |
| 71 | Mike Holmes | 27 | 2010-2013 | |
| 71 | Grant Hutson | 27 | 2042-2043 | |
| 71 | Sloan Ljoekelsoey | 27 | 2033-2035 | |
| 71 | Declan Ogles# | 27 | 2046-2047 | |
| 71 | Joe Pedersen | 27 | 2020-2023 | |
| 71 | Maximiano Pilatos | 27 | 2022-2025 | |
| 71 | Ismael Rodriguez | 27 | 2013-2016 | |
| 71 | Antonio Salinas | 27 | 2015-2019 | |
| 71 | K.J. Starling | 27 | 2034-2035 | |
| 71 | Jakob Taylor# | 27 | 2039-2040 | |
| 71 | Richard Thiele | 27 | 2017-2021 | |
| 71 | Steve Welch | 27 | 2039-2041 | |
| 88 | Scott Andrews | 26 | 2007-2012 | |
| 88 | Hunter Aris# | 26 | 2047-2049 | |
| 88 | Amaral Arrieta | 26 | 2037-2040 | |
| 88 | Ramon Ayala | 26 | 2014-2018 | |
| 88 | Matt Burgess | 26 | 2008-2010 | |
| 88 | Bryan Court | 26 | 2015-2020 | |
| 88 | Alfredo Flores | 26 | 2008-2012 | |
| 88 | Jose Gonzalez | 26 | 2015-2019 | |
| 88 | Rick Hanson | 26 | 2028-2032 | |
| 88 | Jameson Jancik | 26 | 2033-2034 | |
| 88 | Dennis Kingsbury | 26 | 2034-2037 | |
| 88 | Hector Medina | 26 | 2023-2026 | |
| 88 | Victor Melendez | 26 | 2014-2017 |
