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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Leo Medina | 70 | 2000-2009 | |
| 2 | Gil Johnson | 68 | 2000-2010 | |
| 2 | Danny Justice | 68 | 2000-2010 | |
| 2 | Devin Nisbet | 68 | 2001-2013 | |
| 5 | Sergio Hernandez | 62 | 2001-2013 | |
| 6 | Josh Hoffman | 59 | 2010-2014 | |
| 7 | Phil Goodman | 58 | 2013-2018 | |
| 8 | Kyle Chamberlin# | 54 | 2013-2020 | |
| 8 | Josh Graham | 54 | 2014-2018 | |
| 8 | Tony Hernandez | 54 | 2000-2010 | |
| 8 | Guo Liu | 54 | 2003-2010 | |
| 12 | Ryan Iverson | 53 | 2001-2007 | |
| 13 | Mike Johnson | 52 | 2004-2009 | |
| 14 | Alexis Hernandez | 51 | 2007-2013 | |
| 15 | Mike Palmer | 50 | 2000-2010 | |
| 16 | Jon Johnson | 48 | 2011-2015 | |
| 16 | Jesus Quintero | 48 | 2007-2010 | |
| 16 | Jose Rios | 48 | 2007-2016 | |
| 19 | Jonathan Aldama | 47 | 2007-2014 | |
| 19 | Joel Atkinson# | 47 | 2012-2019 | |
| 19 | Dragutin Sujic | 47 | 2002-2013 | |
| 22 | Sean Hickey | 46 | 2003-2010 | |
| 22 | Olivier Philibert | 46 | 2002-2010 | |
| 24 | Jesse Bettinger | 45 | 2000-2010 | |
| 24 | Jesse Parker | 45 | 2000-2009 | |
| 24 | John Wendel | 45 | 2010-2015 | |
| 27 | Danny Adame | 44 | 2000-2006 | |
| 27 | Silvestro Cilento | 44 | 2012-2016 | |
| 27 | Brian O'Connor | 44 | 2000-2006 | |
| 27 | Jose Rivera | 44 | 2000-2012 | |
| 31 | Bill Mitchell | 43 | 2013-2018 | |
| 31 | Mario Pellot | 43 | 2000-2003 | |
| 31 | John Pyles# | 43 | 2016-2019 | |
| 34 | Robert Garcia# | 42 | 2015-2020 | |
| 34 | Willie Lopez | 42 | 2006-2011 | |
| 34 | Brendan Rees | 42 | 2001-2010 | |
| 34 | Jaden Taylor | 42 | 2005-2013 | |
| 38 | Isaiah Gunter | 41 | 2008-2014 | |
| 38 | Ronnie Roberson# | 41 | 2014-2020 | |
| 40 | Albert Espinoza# | 40 | 2017-2020 | |
| 40 | Jason Puente | 40 | 2010-2016 | |
| 40 | Marcos Sanchez | 40 | 2000-2008 | |
| 43 | John Doty# | 39 | 2016-2019 | |
| 43 | Jesus Mares | 39 | 2000-2010 | |
| 43 | Ricky Matta | 39 | 2005-2013 | |
| 43 | Kevin Tolbert | 39 | 2006-2013 | |
| 47 | Greg Flyer | 38 | 2000-2012 | |
| 47 | Joe St. Clair | 38 | 2006-2015 | |
| 47 | George Wilson# | 38 | 2015-2020 | |
| 50 | Vsevolod Debalyuk | 37 | 2012-2016 | |
| 50 | Guillermo Lugo | 37 | 2000-2007 | |
| 50 | Miguel Sosa | 37 | 2000-2006 | |
| 53 | Ryan Alred | 36 | 2010-2014 | |
| 53 | Chris Barrionuevo | 36 | 2004-2011 | |
| 53 | Jerry Lopez | 36 | 2000-2006 | |
| 53 | Rafael Martinez | 36 | 2006-2014 | |
| 53 | Omar Munoz | 36 | 2003-2009 | |
| 53 | Enrique Perez# | 36 | 2007-2020 | |
| 53 | Scott Reyes | 36 | 2008-2014 | |
| 60 | Keisuke Deshimaru# | 35 | 2013-2020 | |
| 60 | Brian Lea | 35 | 2001-2010 | |
| 60 | Jesse Malone | 35 | 2004-2009 | |
| 60 | Yukichi Nishida | 35 | 2008-2014 | |
| 64 | Matt Barker | 34 | 2007-2010 | |
| 64 | Juan Cabera | 34 | 2000-2008 | |
| 64 | Pascal Clément | 34 | 2000-2006 | |
| 64 | Albert Fabian# | 34 | 2012-2013 | |
| 64 | Daniel Harris | 34 | 2012-2015 | |
| 64 | Chris Maldonado | 34 | 2005-2012 | |
| 64 | Ricardo Manzanares | 34 | 2003-2007 | |
| 64 | Victor Medina | 34 | 2005-2014 | |
| 64 | Mario Santos# | 34 | 2013-2020 | |
| 64 | Juan Sauceda# | 34 | 2016-2020 | |
| 64 | Joe Stanley# | 34 | 2016-2018 | |
| 64 | Antonio Suarez | 34 | 2007-2016 | |
| 64 | Luis Torres | 34 | 2000-2012 | |
| 77 | Jaheem Brown# | 33 | 2015-2020 | |
| 77 | Colin Cox | 33 | 2005-2010 | |
| 77 | Mike Davis# | 33 | 2015-2020 | |
| 77 | Arturo Jimenez | 33 | 2000-2004 | |
| 77 | Frank Rodriguez | 33 | 2010-2018 | |
| 77 | Marco Sandoval | 33 | 2012-2018 | |
| 77 | Jose Tirado | 33 | 2003-2010 | |
| 77 | Pedro Vigil | 33 | 2000-2009 | |
| 85 | Mario Castillon | 32 | 2000-2007 | |
| 85 | Oscar Castoire# | 32 | 2009-2019 | |
| 85 | Dave Cole | 32 | 2000-2009 | |
| 85 | Nate Hendrickson | 32 | 2000-2007 | |
| 85 | Ryosuke Hosaka | 32 | 2000-2009 | |
| 85 | John Johnson | 32 | 2007-2014 | |
| 85 | Leo Perez | 32 | 2005-2013 | |
| 85 | Ivan Salgado | 32 | 2014-2018 | |
| 85 | Adam Webb | 32 | 2001-2006 | |
| 94 | Angel Aragon | 31 | 2015-2019 | |
| 94 | Rick David | 31 | 2011-2016 | |
| 94 | Guillermo de la Cruz | 31 | 2014-2019 | |
| 94 | Adam Haire | 31 | 2017-2019 | |
| 94 | Gabriel Jordan | 31 | 2000-2006 | |
| 94 | Dylan King | 31 | 2015-2018 | |
| 94 | Brian Madison# | 31 | 2014-2019 |
