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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Fox Mulder | 39 | 2007-2012 | |
| 2 | Gary Harris | 33 | 2000-2003 | |
| 3 | Luke Mayfield | 31 | 2005-2008 | |
| 4 | Alejandro Ramos | 29 | 2011-2015 | |
| 5 | Josh Benez | 28 | 2004-2009 | |
| 5 | Scot Dunn | 28 | 2006-2010 | |
| 5 | Steve Hoffman* | 28 | 2006-2010 | |
| 8 | Alfred Childress# | 27 | 2052-2057 | |
| 8 | Richard Mazzola | 27 | 2004-2008 | |
| 8 | Bill Rhodes | 27 | 2003-2007 | |
| 11 | Justin Alexander, Jr. | 26 | 2007-2011 | |
| 11 | Boyd Milicent | 26 | 2006-2010 | |
| 11 | George Smith Patton | 26 | 2002-2006 | |
| 11 | António Rodríguez | 26 | 2005-2009 | |
| 15 | Jesús Gonzáles | 25 | 2016-2020 | |
| 15 | Bobby Guthrington | 25 | 2011-2015 | |
| 15 | Yann Manfredi | 25 | 2005-2009 | |
| 15 | Bob Martin | 25 | 2002-2005 | |
| 19 | José Aicón | 24 | 2005-2009 | |
| 19 | Julian Anderson | 24 | 2005-2009 | |
| 19 | Morris Brown | 24 | 1998-2001 | |
| 19 | Juan Lucero | 24 | 2011-2015 | |
| 19 | Joe Miller | 24 | 2003-2007 | |
| 19 | Charlie Prince | 24 | 2014-2017 | |
| 19 | Pat Rice | 24 | 2004-2008 | |
| 26 | Javier Alejo | 23 | 2000-2003 | |
| 26 | Uriah Colon | 23 | 2006-2010 | |
| 26 | Peter Dean# | 23 | 2040-2045 | |
| 26 | José Hernández | 23 | 1999-2002 | |
| 26 | Mike Hibbard | 23 | 2009-2013 | |
| 26 | Chad Jones | 23 | 2014-2017 | |
| 26 | Miguel Lara | 23 | 2011-2015 | |
| 26 | Scott Walker | 23 | 2009-2013 | |
| 34 | Zach Bauer | 22 | 2003-2007 | |
| 34 | Nick Clayton | 22 | 2008-2011 | |
| 34 | Gill Frasquilho | 22 | 2004-2008 | |
| 34 | Juan García# | 22 | 2053-2057 | |
| 34 | Fei-hsien Hang# | 22 | 2053-2057 | |
| 34 | Allen Kennedy | 22 | 2003-2006 | |
| 34 | José León | 22 | 2012-2015 | |
| 34 | Darren Marshall | 22 | 2010-2014 | |
| 34 | Ramón Mendoza | 22 | 2014-2017 | |
| 34 | Henri Mignot# | 22 | 2052-2057 | |
| 34 | Luis Tiant IV | 22 | 2008-2011 | |
| 34 | Armando Vela# | 22 | 2052-2057 | |
| 34 | Cal Wilson | 22 | 2000-2003 | |
| 47 | Daniel Bailey | 21 | 2001-2004 | |
| 47 | Li Beggs | 21 | 2016-2018 | |
| 47 | Ricky Breshear | 21 | 1999-2003 | |
| 47 | Gabriel Chávez | 21 | 2003-2007 | |
| 47 | Bill Harris | 21 | 2016-2019 | |
| 47 | Ye Kung | 21 | 2018-2022 | |
| 47 | Alfonso Martínez | 21 | 2011-2014 | |
| 47 | Tony Riley | 21 | 2003-2007 | |
| 47 | Enrique Rivera | 21 | 2015-2018 | |
| 47 | Jim Schroeder | 21 | 2010-2013 | |
| 47 | Javier Soto | 21 | 2003-2007 | |
| 47 | Barney Stinson | 21 | 2002-2005 | |
| 47 | David West | 21 | 2006-2010 | |
| 47 | Greg Wood | 21 | 2008-2012 | |
| 47 | Scott Young | 21 | 2009-2013 | |
| 62 | Jesús Aguirre | 20 | 2009-2013 | |
| 62 | Dillon Bell | 20 | 2011-2014 | |
| 62 | Curt Clark | 20 | 2007-2011 | |
| 62 | Luis Freitas | 20 | 2010-2014 | |
| 62 | Michael Jones | 20 | 2005-2009 | |
| 62 | Julián Martínez | 20 | 2012-2015 | |
| 62 | Luis Miguel Medina | 20 | 2033-2038 | |
| 62 | Jason Morris | 20 | 2021-2024 | |
| 62 | Patrick O'Malley | 20 | 2007-2011 | |
| 62 | Javier Pérez | 20 | 2000-2003 | |
| 62 | Víctor Quiñonez | 20 | 2012-2015 | |
| 62 | Jatinder Rajal | 20 | 2011-2015 | |
| 62 | Mario Ramos | 20 | 2010-2013 | |
| 62 | Miguel Angel Serrano | 20 | 2001-2004 | |
| 62 | Marcos Sierra | 20 | 2006-2010 | |
| 62 | Héctor Velásquez | 20 | 1998-2001 | |
| 78 | Mark Bacon | 19 | 2003-2006 | |
| 78 | John David Busfield | 19 | 2002-2004 | |
| 78 | Will Craig | 19 | 2001-2003 | |
| 78 | Bartolo Cruz | 19 | 2016-2019 | |
| 78 | António Estrada | 19 | 2008-2011 | |
| 78 | Luis Flores | 19 | 2001-2004 | |
| 78 | Augusto García | 19 | 2003-2006 | |
| 78 | Tadanobu Ine | 19 | 2001-2003 | |
| 78 | Grux King | 19 | 2005-2009 | |
| 78 | Trent Kirkpatrick# | 19 | 2052-2057 | |
| 78 | José Lara | 19 | 1999-2002 | |
| 78 | Alberto Magana | 19 | 2020-2023 | |
| 78 | John Miller | 19 | 1999-2001 | |
| 78 | Robert Oliver | 19 | 2021-2024 | |
| 78 | Richard Phillips | 19 | 2004-2008 | |
| 78 | Ramón Ramírez | 19 | 2010-2014 | |
| 78 | Miguel Rivera | 19 | 2001-2004 | |
| 78 | Sam Rutgers# | 19 | 2045-2047 | |
| 78 | Jamie Sisson | 19 | 2005-2008 | |
| 78 | James Smith | 19 | 2000-2003 | |
| 78 | Sergio Souza | 19 | 2020-2023 | |
| 78 | Jason Taylor | 19 | 2007-2011 | |
| 78 | Stevie Wolarski | 19 | 2009-2012 |
