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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 | |
| 5 | Casey Levy# | 62 | 2018-2025 | |
| 7 | Kyle Chamberlin | 59 | 2013-2021 | |
| 7 | Josh Hoffman | 59 | 2010-2014 | |
| 9 | Phil Goodman | 58 | 2013-2018 | |
| 10 | Jesus Garcia | 56 | 2018-2025 | |
| 11 | Enrique Perez | 55 | 2007-2023 | |
| 12 | Joel Atkinson | 54 | 2012-2021 | |
| 12 | Josh Graham | 54 | 2014-2018 | |
| 12 | Tony Hernandez | 54 | 2000-2010 | |
| 12 | Guo Liu | 54 | 2003-2010 | |
| 12 | Ronnie Roberson | 54 | 2014-2021 | |
| 17 | Ryan Iverson | 53 | 2001-2007 | |
| 18 | Mike Johnson | 52 | 2004-2009 | |
| 19 | Alexis Hernandez | 51 | 2007-2013 | |
| 20 | Albert Espinoza | 50 | 2017-2021 | |
| 20 | Mike Palmer | 50 | 2000-2010 | |
| 22 | Jimmy Grams# | 49 | 2016-2026 | |
| 22 | Matt Hanna# | 49 | 2021-2026 | |
| 24 | Jon Johnson | 48 | 2011-2015 | |
| 24 | Jesus Quintero | 48 | 2007-2010 | |
| 24 | Jose Rios | 48 | 2007-2016 | |
| 27 | Jonathan Aldama | 47 | 2007-2014 | |
| 27 | Ed Jenkins# | 47 | 2013-2023 | |
| 27 | Dragutin Sujic | 47 | 2002-2013 | |
| 30 | Sean Hickey | 46 | 2003-2010 | |
| 30 | Josh Oakman# | 46 | 2018-2022 | |
| 30 | Olivier Philibert | 46 | 2002-2010 | |
| 33 | Jesse Bettinger | 45 | 2000-2010 | |
| 33 | Jesse Parker | 45 | 2000-2009 | |
| 33 | John Wendel | 45 | 2010-2015 | |
| 36 | Danny Adame | 44 | 2000-2006 | |
| 36 | Silvestro Cilento | 44 | 2012-2016 | |
| 36 | Brian O'Connor | 44 | 2000-2006 | |
| 36 | Jose Rivera | 44 | 2000-2012 | |
| 36 | Jimmy Torres | 44 | 2017-2023 | |
| 41 | Bill Mitchell | 43 | 2013-2018 | |
| 41 | Mario Pellot | 43 | 2000-2003 | |
| 41 | John Pyles | 43 | 2016-2019 | |
| 44 | Robert Garcia | 42 | 2015-2020 | |
| 44 | Willie Lopez | 42 | 2006-2011 | |
| 44 | Brendan Rees | 42 | 2001-2010 | |
| 44 | Jaden Taylor | 42 | 2005-2013 | |
| 48 | Isaiah Gunter | 41 | 2008-2014 | |
| 48 | Jonathan Malcolm | 41 | 2018-2021 | |
| 48 | Lílian Pona | 41 | 2015-2021 | |
| 48 | Jose Rivera | 41 | 2020-2023 | |
| 52 | Jose Perez# | 40 | 2021-2024 | |
| 52 | Jason Puente | 40 | 2010-2016 | |
| 52 | Marcos Sanchez | 40 | 2000-2008 | |
| 55 | John Doty | 39 | 2016-2019 | |
| 55 | Jesus Mares | 39 | 2000-2010 | |
| 55 | Ricky Matta | 39 | 2005-2013 | |
| 55 | Kevin Tolbert | 39 | 2006-2013 | |
| 59 | Greg Flyer | 38 | 2000-2012 | |
| 59 | Danny Pena# | 38 | 2015-2024 | |
| 59 | Joe St. Clair | 38 | 2006-2015 | |
| 59 | George Wilson | 38 | 2015-2021 | |
| 63 | Bobby Carrero# | 37 | 2022-2026 | |
| 63 | Joel Daniels# | 37 | 2014-2025 | |
| 63 | Vsevolod Debalyuk | 37 | 2012-2016 | |
| 63 | Guillermo Lugo | 37 | 2000-2007 | |
| 63 | Jeff Sharp# | 37 | 2020-2023 | |
| 63 | Miguel Sosa | 37 | 2000-2006 | |
| 69 | Ryan Alred | 36 | 2010-2014 | |
| 69 | Chris Barrionuevo | 36 | 2004-2011 | |
| 69 | Jerry Lopez | 36 | 2000-2006 | |
| 69 | Rafael Martinez | 36 | 2006-2014 | |
| 69 | Omar Munoz | 36 | 2003-2009 | |
| 69 | Scott Reyes | 36 | 2008-2014 | |
| 75 | Keisuke Deshimaru | 35 | 2013-2020 | |
| 75 | Brian Lea | 35 | 2001-2010 | |
| 75 | Jesse Malone | 35 | 2004-2009 | |
| 75 | Yukichi Nishida | 35 | 2008-2014 | |
| 79 | Matt Barker | 34 | 2007-2010 | |
| 79 | Juan Cabera | 34 | 2000-2008 | |
| 79 | Pascal Clément | 34 | 2000-2006 | |
| 79 | Albert Fabian# | 34 | 2012-2013 | |
| 79 | Daniel Harris | 34 | 2012-2015 | |
| 79 | Chris Maldonado | 34 | 2005-2012 | |
| 79 | Ricardo Manzanares | 34 | 2003-2007 | |
| 79 | Victor Medina | 34 | 2005-2014 | |
| 79 | Angelo Quezada# | 34 | 2022-2026 | |
| 79 | Mario Santos | 34 | 2013-2020 | |
| 79 | Juan Sauceda | 34 | 2016-2020 | |
| 79 | Joe Stanley | 34 | 2016-2018 | |
| 79 | Antonio Suarez | 34 | 2007-2016 | |
| 79 | Luis Torres | 34 | 2000-2012 | |
| 93 | Jaheem Brown | 33 | 2015-2020 | |
| 93 | Mike Brown# | 33 | 2021-2026 | |
| 93 | Mike Carachure | 33 | 2010-2021 | |
| 93 | Colin Cox | 33 | 2005-2010 | |
| 93 | Mike Davis | 33 | 2015-2020 | |
| 93 | Jon Escobar# | 33 | 2023-2026 | |
| 93 | Juan Fernandez | 33 | 2013-2021 | |
| 93 | Jordan Gaines | 33 | 2020-2025 |
