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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Eric Burdine | 11 | 2000-2017 | |
| 1 | Cody Morosko | 11 | 2000-2010 | |
| 3 | Corey Gruver# | 10 | 2006-2021 | |
| 4 | Xiang-ling Fei* | 9 | 2000-2012 | |
| 4 | Paul Ledford* | 9 | 2000-2013 | |
| 4 | Jonathan Luna | 9 | 2000-2011 | |
| 4 | Heriberto Milan# | 9 | 2007-2021 | |
| 8 | Gordie Clifford# | 8 | 2013-2021 | |
| 8 | Chris Mattison# | 8 | 2012-2019 | |
| 8 | Rodolfo Soto# | 8 | 2015-2021 | |
| 11 | Blake Barber | 7 | 2000-2007 | |
| 11 | Josh Flaten# | 7 | 2015-2021 | |
| 11 | Johnny Keener# | 7 | 2015-2021 | |
| 11 | Chad Landreth | 7 | 2001-2017 | |
| 11 | Rodrigo Lemus# | 7 | 2013-2021 | |
| 11 | Jose Rodriguez* | 7 | 2000-2016 | |
| 17 | Francisco Camacho | 6 | 2000-2013 | |
| 17 | Jordan Clarke# | 6 | 2004-2021 | |
| 17 | Albert Fabian# | 6 | 2014-2021 | |
| 17 | Sukeaki Kato | 6 | 2001-2014 | |
| 17 | Tom Kitko# | 6 | 2012-2021 | |
| 17 | Bill Vasquez | 6 | 2000-2012 | |
| 23 | Bill Flowers# | 5 | 2011-2021 | |
| 23 | Joe Hart# | 5 | 2013-2021 | |
| 23 | Jack Ivory# | 5 | 2018-2021 | |
| 23 | Corey Johnson | 5 | 2010-2020 | |
| 23 | Iliana Preciado | 5 | 2000-2009 | |
| 23 | Brian Prince# | 5 | 2011-2021 | |
| 23 | Greg Sandlin# | 5 | 2009-2021 | |
| 23 | Chad Stokes | 5 | 2006-2017 | |
| 23 | Alfredo Tiscareno# | 5 | 2010-2021 | |
| 32 | Casey Abbott# | 4 | 2009-2021 | |
| 32 | Sean Bartol | 4 | 2000-2010 | |
| 32 | Adam Farmer | 4 | 2000-2009 | |
| 32 | Chris Frost# | 4 | 2011-2021 | |
| 32 | Miles Hale | 4 | 2000-2011 | |
| 32 | Yosaburo Kanda# | 4 | 2013-2021 | |
| 32 | Santos Martinez | 4 | 2000-2012 | |
| 32 | Carlos Mendez# | 4 | 2011-2021 | |
| 32 | Emmanuel Mendoza# | 4 | 2008-2021 | |
| 32 | Du-sung Moon | 4 | 2002-2015 | |
| 32 | Elard Nijhuis | 4 | 2000-2009 | |
| 32 | Pat Payne# | 4 | 2009-2021 | |
| 32 | Adrian Radecki# | 4 | 2012-2019 | |
| 32 | Julian Rangel | 4 | 2008-2018 | |
| 32 | Matt Schmid# | 4 | 2013-2021 | |
| 32 | Shawn Spruce | 4 | 2007-2016 | |
| 32 | Aaron Sutton | 4 | 2009-2021 | |
| 32 | Travis Thurber# | 4 | 2005-2021 | |
| 50 | Lorenzo Andrade# | 3 | 2016-2021 | |
| 50 | Justin Armstrong | 3 | 2000-2006 | |
| 50 | William Arredondo | 3 | 2000-2012 | |
| 50 | Ron Baumgardner | 3 | 2010-2019 | |
| 50 | Miguel Berrios# | 3 | 2018-2021 | |
| 50 | Marty Capone# | 3 | 2019-2021 | |
| 50 | Oreste Comollo | 3 | 2001-2014 | |
| 50 | Adam D'Alberto# | 3 | 2016-2021 | |
| 50 | Seth Dann | 3 | 2002-2013 | |
| 50 | Brett Dorman | 3 | 2005-2019 | |
| 50 | Geremia Farinelli | 3 | 2000-2014 | |
| 50 | Mickey Ferrell# | 3 | 2011-2021 | |
| 50 | Carlos Garcia | 3 | 2000-2014 | |
| 50 | Ken Goers | 3 | 2001-2014 | |
| 50 | Phil Gregoire# | 3 | 2013-2021 | |
| 50 | Travis Gross# | 3 | 2014-2021 | |
| 50 | Mike Hill | 3 | 2001-2011 | |
| 50 | Chris Jacoby# | 3 | 2015-2021 | |
| 50 | Grant Lee# | 3 | 2014-2021 | |
| 50 | Sergio Maffi | 3 | 2000-2010 | |
| 50 | Hethum Manasarian | 3 | 2001-2020 | |
| 50 | Oscar Martinez | 3 | 2000-2010 | |
| 50 | Sergio Martinez | 3 | 2005-2017 | |
| 50 | Juan Mendoza# | 3 | 2014-2021 | |
| 50 | Dan Mills# | 3 | 2014-2021 | |
| 50 | Izzy Montano | 3 | 2000-2010 | |
| 50 | Jose Moreno | 3 | 2000-2014 | |
| 50 | Lee Morgan# | 3 | 2019-2021 | |
| 50 | David Nations | 3 | 2000-2008 | |
| 50 | Mike Nave | 3 | 2009-2017 | |
| 50 | Ben O'Halloran# | 3 | 2016-2021 | |
| 50 | Carlos Pardo# | 3 | 2012-2021 | |
| 50 | Brian Rohde | 3 | 2009-2020 | |
| 50 | Willie Sanchez | 3 | 2000-2011 | |
| 50 | Scott Schowalter# | 3 | 2012-2021 | |
| 50 | Miguel Soto# | 3 | 2013-2021 | |
| 50 | Stephen Stride# | 3 | 2011-2020 | |
| 50 | Tommy Swift# | 3 | 2019-2021 | |
| 50 | Kory Tourville# | 3 | 2014-2021 | |
| 50 | Justin Turbeville | 3 | 2008-2018 | |
| 50 | Keith Young | 3 | 2000-2007 | |
| 50 | Kyle Ziegler | 3 | 2000-2011 | |
| 92 | Vance Adams | 2 | 2000-2013 | |
| 92 | Tomas Adon | 2 | 2004-2018 | |
| 92 | Richard Alter# | 2 | 2019-2021 | |
| 92 | Felipe Ayala# | 2 | 2013-2021 | |
| 92 | Austin Bauer | 2 | 2005-2014 | |
| 92 | Ben Baxter | 2 | 2000-2010 | |
| 92 | Chris Bentley | 2 | 2008-2020 | |
| 92 | Julian Bryant# | 2 | 2020-2021 | |
| 92 | Seth Carey | 2 | 2004-2016 |
