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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Jim Martino | 54 | 2003-2010 | |
| 2 | Mike Mayes# | 48 | 2016-2020 | |
| 3 | Seung-woo Park# | 47 | 2015-2020 | |
| 4 | Dane Terry | 46 | 2013-2016 | |
| 5 | Mario Gomez | 45 | 2003-2013 | |
| 6 | Guadalupe Moranchel | 44 | 2003-2009 | |
| 7 | Eric Cochran | 43 | 2006-2011 | |
| 7 | Fred Watson | 43 | 2001-2007 | |
| 9 | Josh Brewer | 42 | 2011-2017 | |
| 10 | Matt Carpenter | 41 | 2012-2017 | |
| 10 | Cameron Ciccaglione | 41 | 2009-2014 | |
| 10 | Tony Laclair | 41 | 2010-2015 | |
| 13 | Jose Alvarez | 40 | 2003-2007 | |
| 13 | Dakota Clayton | 40 | 2000-2004 | |
| 13 | Rick Harmon | 40 | 2000-2005 | |
| 13 | Jose Medrano | 40 | 2001-2007 | |
| 17 | Dennis Allen# | 39 | 2018-2020 | |
| 17 | Izzy Aranda# | 39 | 2014-2018 | |
| 17 | Denny Arizpe | 39 | 2000-2018 | |
| 17 | Gil Morales | 39 | 2007-2014 | |
| 21 | Andy Alger | 38 | 2012-2014 | |
| 21 | John Hall | 38 | 2000-2006 | |
| 21 | Spencer James | 38 | 2014-2018 | |
| 21 | Justin Ostrovsky | 38 | 2000-2005 | |
| 25 | Axel DeMeo# | 37 | 2015-2020 | |
| 25 | Ian Hutchinson | 37 | 2014-2016 | |
| 25 | Jordan Otero | 37 | 2010-2015 | |
| 25 | Steve Parent | 37 | 2012-2018 | |
| 25 | Tom Parson | 37 | 2000-2009 | |
| 30 | Gabriel Huey# | 36 | 2016-2019 | |
| 30 | Larry Voltaire | 36 | 2000-2005 | |
| 30 | Kevin Yoder | 36 | 2001-2008 | |
| 33 | Reynaldo Cordero | 35 | 2008-2014 | |
| 33 | Raul Mantilla | 35 | 2001-2006 | |
| 33 | Carlos Mendez | 35 | 2004-2012 | |
| 36 | Ivan Gonzalez | 34 | 2005-2008 | |
| 36 | Gavin Hornbeck | 34 | 2013-2016 | |
| 36 | Tony Jimenez | 34 | 2000-2004 | |
| 36 | Dustin Jones# | 34 | 2015-2019 | |
| 36 | Jesus Luna# | 34 | 2016-2020 | |
| 36 | Jesse Malone | 34 | 2000-2007 | |
| 36 | Will Parker | 34 | 2002-2007 | |
| 36 | Alex Perez# | 34 | 2016-2020 | |
| 44 | Jonathan Bravo# | 33 | 2015-2020 | |
| 44 | Danny Linares | 33 | 2009-2017 | |
| 44 | Matt O'Bryan | 33 | 2000-2005 | |
| 44 | Enrique Ponce | 33 | 2001-2005 | |
| 48 | Marc Acevedo | 32 | 2000-2004 | |
| 48 | George Chavies | 32 | 2000-2004 | |
| 48 | Jake Davis | 32 | 2001-2006 | |
| 48 | Gil Martinez# | 32 | 2014-2018 | |
| 48 | Trevor Moses# | 32 | 2014-2020 | |
| 53 | Hector Dimiceli | 31 | 2005-2009 | |
| 53 | Nate Evangelista | 31 | 2010-2014 | |
| 53 | Aaron Ewing# | 31 | 2014-2019 | |
| 53 | Nick Hensley | 31 | 2000-2010 | |
| 53 | Jason Humphrey | 31 | 2010-2014 | |
| 53 | Jared Jones# | 31 | 2018-2020 | |
| 53 | Larry Klisch | 31 | 2011-2016 | |
| 53 | Joel Larmon | 31 | 2001-2008 | |
| 53 | Mel Quintero | 31 | 2012-2014 | |
| 53 | Jose Ramirez | 31 | 2011-2015 | |
| 53 | Eddie Saldana | 31 | 2011-2016 | |
| 53 | Scott Sauer# | 31 | 2018-2020 | |
| 53 | Cory Thompson | 31 | 2000-2006 | |
| 66 | Alex Diego | 30 | 2010-2014 | |
| 66 | William DiPaola | 30 | 2000-2004 | |
| 66 | Danny Justice | 30 | 2006-2010 | |
| 66 | Danny Melendez | 30 | 2010-2014 | |
| 66 | Eric Pacheco | 30 | 2005-2015 | |
| 66 | Leo Perez | 30 | 2005-2014 | |
| 66 | Mike Salazar | 30 | 2000-2005 | |
| 66 | Pat Sherman | 30 | 2013-2017 | |
| 66 | David Silva | 30 | 2015-2018 | |
| 75 | Javy Castro | 29 | 2010-2015 | |
| 75 | Manny Cruz | 29 | 2008-2014 | |
| 75 | Chris Culver | 29 | 2001-2005 | |
| 75 | Casey Felice | 29 | 2000-2004 | |
| 75 | Mike Friedrich | 29 | 2001-2010 | |
| 75 | Roberto Hurtado# | 29 | 2014-2020 | |
| 75 | Billy LaBry | 29 | 2006-2014 | |
| 75 | Jose Lopez | 29 | 2009-2015 | |
| 75 | Mike Montoya# | 29 | 2012-2016 | |
| 75 | Alejandro Velez | 29 | 2003-2009 | |
| 85 | Andrew Chalmers# | 28 | 2014-2015 | |
| 85 | Tim Darden | 28 | 2010-2014 | |
| 85 | Trevor de Graaf | 28 | 2000-2004 | |
| 85 | Dale Larson | 28 | 2013-2018 | |
| 85 | Ricky Mena# | 28 | 2018-2020 | |
| 85 | Matthew Mosley | 28 | 2005-2013 | |
| 85 | Ramon Perez | 28 | 2003-2006 | |
| 92 | Travis Brown# | 27 | 2017-2019 | |
| 92 | Mike Carachure# | 27 | 2010-2016 | |
| 92 | Chris Carey | 27 | 2000-2002 | |
| 92 | Rich Elliott | 27 | 2000-2003 | |
| 92 | Jesse Erickson | 27 | 2001-2010 | |
| 92 | Cesar Escobedo# | 27 | 2016-2018 | |
| 92 | Tony Gomez | 27 | 2001-2011 | |
| 92 | Sergio Gonzales | 27 | 2014-2016 | |
| 92 | Oscar Hernandez# | 27 | 2014-2020 |
