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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Mike Mayes# | 64 | 2016-2021 | |
| 2 | Jim Martino | 54 | 2003-2010 | |
| 3 | Scott Sauer# | 49 | 2018-2022 | |
| 4 | Seung-woo Park# | 47 | 2015-2020 | |
| 5 | Dane Terry | 46 | 2013-2016 | |
| 6 | Mario Gomez | 45 | 2003-2013 | |
| 7 | Guadalupe Moranchel | 44 | 2003-2009 | |
| 8 | Eric Cochran | 43 | 2006-2011 | |
| 8 | Cesar Escobedo# | 43 | 2016-2021 | |
| 8 | Fred Watson | 43 | 2001-2007 | |
| 11 | Josh Brewer | 42 | 2011-2017 | |
| 11 | Scott Staffieri# | 42 | 2016-2022 | |
| 13 | Joe Brackett# | 41 | 2018-2022 | |
| 13 | Matt Carpenter | 41 | 2012-2017 | |
| 13 | Cameron Ciccaglione | 41 | 2009-2014 | |
| 13 | Tony Laclair | 41 | 2010-2015 | |
| 17 | Jose Alvarez | 40 | 2003-2007 | |
| 17 | Dakota Clayton | 40 | 2000-2004 | |
| 17 | Rick Harmon | 40 | 2000-2005 | |
| 17 | Jared Jones# | 40 | 2018-2021 | |
| 17 | Jose Medrano | 40 | 2001-2007 | |
| 22 | Dennis Allen# | 39 | 2018-2020 | |
| 22 | Izzy Aranda | 39 | 2014-2018 | |
| 22 | Denny Arizpe | 39 | 2000-2018 | |
| 22 | Gil Morales | 39 | 2007-2014 | |
| 26 | Andy Alger | 38 | 2012-2014 | |
| 26 | John Hall | 38 | 2000-2006 | |
| 26 | Spencer James | 38 | 2014-2018 | |
| 26 | Justin Ostrovsky | 38 | 2000-2005 | |
| 30 | Axel DeMeo | 37 | 2015-2020 | |
| 30 | Steve Hill# | 37 | 2015-2022 | |
| 30 | Ian Hutchinson | 37 | 2014-2016 | |
| 30 | Jordan Otero | 37 | 2010-2015 | |
| 30 | Steve Parent | 37 | 2012-2018 | |
| 30 | Tom Parson | 37 | 2000-2009 | |
| 36 | Gabriel Huey | 36 | 2016-2019 | |
| 36 | Larry Voltaire | 36 | 2000-2005 | |
| 36 | Kevin Yoder | 36 | 2001-2008 | |
| 39 | Reynaldo Cordero | 35 | 2008-2014 | |
| 39 | Raul Mantilla | 35 | 2001-2006 | |
| 39 | Carlos Mendez | 35 | 2004-2012 | |
| 42 | Ivan Gonzalez | 34 | 2005-2008 | |
| 42 | Gavin Hornbeck | 34 | 2013-2016 | |
| 42 | Tony Jimenez | 34 | 2000-2004 | |
| 42 | Dustin Jones | 34 | 2015-2019 | |
| 42 | Jesus Luna | 34 | 2016-2020 | |
| 42 | Jesse Malone | 34 | 2000-2007 | |
| 42 | Will Parker | 34 | 2002-2007 | |
| 42 | Alex Perez | 34 | 2016-2020 | |
| 50 | Jonathan Bravo | 33 | 2015-2020 | |
| 50 | Danny Linares | 33 | 2009-2017 | |
| 50 | Danny Martinez# | 33 | 2017-2021 | |
| 50 | Matt O'Bryan | 33 | 2000-2005 | |
| 50 | Enrique Ponce | 33 | 2001-2005 | |
| 50 | Alvaro Salas# | 33 | 2019-2022 | |
| 56 | Marc Acevedo | 32 | 2000-2004 | |
| 56 | Corey Alexander# | 32 | 2017-2021 | |
| 56 | George Chavies | 32 | 2000-2004 | |
| 56 | Jake Davis | 32 | 2001-2006 | |
| 56 | Gil Martinez# | 32 | 2014-2018 | |
| 56 | Trevor Moses# | 32 | 2014-2020 | |
| 62 | Rick Cortez# | 31 | 2017-2022 | |
| 62 | Hector Dimiceli | 31 | 2005-2009 | |
| 62 | Jon Escobar# | 31 | 2019-2022 | |
| 62 | Nate Evangelista | 31 | 2010-2014 | |
| 62 | Aaron Ewing | 31 | 2014-2019 | |
| 62 | Nick Hensley | 31 | 2000-2010 | |
| 62 | Jason Humphrey | 31 | 2010-2014 | |
| 62 | Larry Klisch | 31 | 2011-2016 | |
| 62 | Joel Larmon | 31 | 2001-2008 | |
| 62 | Mel Quintero | 31 | 2012-2014 | |
| 62 | Jose Ramirez | 31 | 2011-2015 | |
| 62 | Eddie Saldana | 31 | 2011-2016 | |
| 62 | Cory Thompson | 31 | 2000-2006 | |
| 75 | Alex Diego | 30 | 2010-2014 | |
| 75 | William DiPaola | 30 | 2000-2004 | |
| 75 | Danny Justice | 30 | 2006-2010 | |
| 75 | Danny Melendez | 30 | 2010-2014 | |
| 75 | Eric Pacheco | 30 | 2005-2015 | |
| 75 | Leo Perez | 30 | 2005-2014 | |
| 75 | Mike Salazar | 30 | 2000-2005 | |
| 75 | Pat Sherman | 30 | 2013-2017 | |
| 75 | David Silva | 30 | 2015-2018 | |
| 84 | Javy Castro | 29 | 2010-2015 | |
| 84 | Manny Cruz | 29 | 2008-2014 | |
| 84 | Chris Culver | 29 | 2001-2005 | |
| 84 | Casey Felice | 29 | 2000-2004 | |
| 84 | Mike Friedrich | 29 | 2001-2010 | |
| 84 | Roberto Hurtado | 29 | 2014-2020 | |
| 84 | Billy LaBry | 29 | 2006-2014 | |
| 84 | Jose Lopez | 29 | 2009-2015 | |
| 84 | John Manship# | 29 | 2021-2022 | |
| 84 | Mike Montoya# | 29 | 2012-2016 | |
| 84 | Ryan Noble# | 29 | 2020-2022 | |
| 84 | Alejandro Velez | 29 | 2003-2009 | |
| 96 | Adam Black# | 28 | 2016-2021 | |
| 96 | Andrew Chalmers | 28 | 2014-2015 | |
| 96 | Kareem Craig# | 28 | 2018-2021 | |
| 96 | Tim Darden | 28 | 2010-2014 | |
| 96 | Trevor de Graaf | 28 | 2000-2004 |
