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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 | Kyle Chamberlin | 59 | 2013-2021 | |
| 6 | Josh Hoffman | 59 | 2010-2014 | |
| 8 | Phil Goodman | 58 | 2013-2018 | |
| 9 | Joel Atkinson | 54 | 2012-2021 | |
| 9 | Josh Graham | 54 | 2014-2018 | |
| 9 | Tony Hernandez | 54 | 2000-2010 | |
| 9 | Guo Liu | 54 | 2003-2010 | |
| 9 | Ronnie Roberson | 54 | 2014-2021 | |
| 14 | Ryan Iverson | 53 | 2001-2007 | |
| 15 | Mike Johnson | 52 | 2004-2009 | |
| 16 | Alexis Hernandez | 51 | 2007-2013 | |
| 17 | Albert Espinoza | 50 | 2017-2021 | |
| 17 | Mike Palmer | 50 | 2000-2010 | |
| 19 | Jon Johnson | 48 | 2011-2015 | |
| 19 | Jesus Quintero | 48 | 2007-2010 | |
| 19 | Jose Rios | 48 | 2007-2016 | |
| 22 | Jonathan Aldama | 47 | 2007-2014 | |
| 22 | Enrique Perez# | 47 | 2007-2022 | |
| 22 | Dragutin Sujic | 47 | 2002-2013 | |
| 25 | Sean Hickey | 46 | 2003-2010 | |
| 25 | Josh Oakman# | 46 | 2018-2022 | |
| 25 | Olivier Philibert | 46 | 2002-2010 | |
| 28 | Jesse Bettinger | 45 | 2000-2010 | |
| 28 | Jesse Parker | 45 | 2000-2009 | |
| 28 | John Wendel | 45 | 2010-2015 | |
| 31 | Danny Adame | 44 | 2000-2006 | |
| 31 | Silvestro Cilento | 44 | 2012-2016 | |
| 31 | Brian O'Connor | 44 | 2000-2006 | |
| 31 | Jose Rivera | 44 | 2000-2012 | |
| 35 | Bill Mitchell | 43 | 2013-2018 | |
| 35 | Mario Pellot | 43 | 2000-2003 | |
| 35 | John Pyles | 43 | 2016-2019 | |
| 38 | Robert Garcia | 42 | 2015-2020 | |
| 38 | Willie Lopez | 42 | 2006-2011 | |
| 38 | Brendan Rees | 42 | 2001-2010 | |
| 38 | Jaden Taylor | 42 | 2005-2013 | |
| 42 | Isaiah Gunter | 41 | 2008-2014 | |
| 42 | Jonathan Malcolm | 41 | 2018-2021 | |
| 42 | Lílian Pona | 41 | 2015-2021 | |
| 42 | Jimmy Torres# | 41 | 2017-2022 | |
| 46 | Jason Puente | 40 | 2010-2016 | |
| 46 | Marcos Sanchez | 40 | 2000-2008 | |
| 48 | John Doty | 39 | 2016-2019 | |
| 48 | Jesus Mares | 39 | 2000-2010 | |
| 48 | Ricky Matta | 39 | 2005-2013 | |
| 48 | Kevin Tolbert | 39 | 2006-2013 | |
| 52 | Greg Flyer | 38 | 2000-2012 | |
| 52 | Joe St. Clair | 38 | 2006-2015 | |
| 52 | George Wilson | 38 | 2015-2021 | |
| 55 | Vsevolod Debalyuk | 37 | 2012-2016 | |
| 55 | Guillermo Lugo | 37 | 2000-2007 | |
| 55 | Miguel Sosa | 37 | 2000-2006 | |
| 58 | Ryan Alred | 36 | 2010-2014 | |
| 58 | Chris Barrionuevo | 36 | 2004-2011 | |
| 58 | Jerry Lopez | 36 | 2000-2006 | |
| 58 | Rafael Martinez | 36 | 2006-2014 | |
| 58 | Omar Munoz | 36 | 2003-2009 | |
| 58 | Scott Reyes | 36 | 2008-2014 | |
| 64 | Keisuke Deshimaru | 35 | 2013-2020 | |
| 64 | Brian Lea | 35 | 2001-2010 | |
| 64 | Jesse Malone | 35 | 2004-2009 | |
| 64 | Yukichi Nishida | 35 | 2008-2014 | |
| 64 | Jose Rivera# | 35 | 2020-2022 | |
| 69 | Matt Barker | 34 | 2007-2010 | |
| 69 | Juan Cabera | 34 | 2000-2008 | |
| 69 | Pascal Clément | 34 | 2000-2006 | |
| 69 | Albert Fabian# | 34 | 2012-2013 | |
| 69 | Daniel Harris | 34 | 2012-2015 | |
| 69 | Ed Jenkins# | 34 | 2013-2022 | |
| 69 | Chris Maldonado | 34 | 2005-2012 | |
| 69 | Ricardo Manzanares | 34 | 2003-2007 | |
| 69 | Victor Medina | 34 | 2005-2014 | |
| 69 | Mario Santos | 34 | 2013-2020 | |
| 69 | Juan Sauceda | 34 | 2016-2020 | |
| 69 | Joe Stanley | 34 | 2016-2018 | |
| 69 | Antonio Suarez | 34 | 2007-2016 | |
| 69 | Luis Torres | 34 | 2000-2012 | |
| 83 | Jaheem Brown | 33 | 2015-2020 | |
| 83 | Mike Carachure | 33 | 2010-2021 | |
| 83 | Colin Cox | 33 | 2005-2010 | |
| 83 | Mike Davis | 33 | 2015-2020 | |
| 83 | Juan Fernandez | 33 | 2013-2021 | |
| 83 | Francisco Gorostieta | 33 | 2015-2021 | |
| 83 | Arturo Jimenez | 33 | 2000-2004 | |
| 83 | Casey Levy# | 33 | 2018-2022 | |
| 83 | Frank Rodriguez | 33 | 2010-2018 | |
| 83 | Marco Sandoval | 33 | 2012-2018 | |
| 83 | Jose Tirado | 33 | 2003-2010 | |
| 83 | Pedro Vigil | 33 | 2000-2009 | |
| 95 | Mario Castillon | 32 | 2000-2007 | |
| 95 | Oscar Castoire | 32 | 2009-2019 | |
| 95 | Dave Cole | 32 | 2000-2009 | |
| 95 | Nate Hendrickson | 32 | 2000-2007 | |
| 95 | Ryosuke Hosaka | 32 | 2000-2009 | |
| 95 | John Johnson | 32 | 2007-2014 |
