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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Chris Patterson | 28 | 2007-2011 | |
| 2 | Toby Ayers# | 25 | 2019-2022 | |
| 3 | Jim Fish | 24 | 2017-2020 | |
| 3 | Gunner MacGruder* | 24 | 2009-2012 | |
| 3 | Avery Parkinson | 24 | 2007-2011 | |
| 3 | António Vega | 24 | 2013-2016 | |
| 7 | Aaron Anderson | 23 | 2011-2014 | |
| 7 | José Patino | 23 | 2009-2012 | |
| 7 | Luis Reyes | 23 | 2015-2018 | |
| 10 | Otto Coleman | 22 | 2015-2018 | |
| 10 | Ernesto Molina | 22 | 2013-2016 | |
| 10 | Tony Ríos | 22 | 2011-2014 | |
| 10 | Alfredo Zambrano | 22 | 2018-2021 | |
| 14 | Denny Lowe | 21 | 2016-2019 | |
| 14 | Melvin McNeal | 21 | 2015-2018 | |
| 14 | Héctor Rivera | 21 | 2016-2019 | |
| 17 | Markus Cameron | 20 | 2015-2018 | |
| 17 | Matt Moody | 20 | 2010-2013 | |
| 19 | Jorge Castillo# | 19 | 2019-2022 | |
| 19 | Joshua Hall | 19 | 2015-2018 | |
| 19 | Michael Johnson | 19 | 2011-2014 | |
| 19 | Marvin Moore | 19 | 2020-2023 | |
| 19 | Paul Norris | 19 | 2013-2016 | |
| 19 | Otis Pearson | 19 | 2016-2019 | |
| 19 | Larry Schultz | 19 | 2009-2012 | |
| 19 | Shoichi Shimizu | 19 | 2011-2014 | |
| 19 | Kevin Thomas | 19 | 2020-2022 | |
| 19 | Ron Wilson# | 19 | 2019-2022 | |
| 29 | Kenny Ashley | 18 | 2011-2014 | |
| 29 | Víctor Carrillo | 18 | 2011-2014 | |
| 29 | Abel Castellanos# | 18 | 2036-2039 | |
| 29 | Walter Daniel# | 18 | 2017-2020 | |
| 29 | Eric Grimes# | 18 | 2034-2037 | |
| 29 | Ben Holman# | 18 | 2025-2028 | |
| 29 | Max Jordan | 18 | 2010-2013 | |
| 29 | Jhong-shun Kong | 18 | 2010-2013 | |
| 29 | Mike Martínez# | 18 | 2036-2039 | |
| 29 | Adrián Navarro | 18 | 2014-2017 | |
| 29 | Mike Randall | 18 | 2019-2022 | |
| 29 | Daniel Sharpe | 18 | 2014-2017 | |
| 41 | Phil Anderson | 17 | 2008-2011 | |
| 41 | Christian Barrett# | 17 | 2034-2037 | |
| 41 | Allen Cook | 17 | 2018-2021 | |
| 41 | Salvador Delozada# | 17 | 2033-2036 | |
| 41 | Ben Ferguson# | 17 | 2036-2039 | |
| 41 | Alberto Flores# | 17 | 2025-2028 | |
| 41 | León Gil | 17 | 2018-2021 | |
| 41 | Christian Hardin# | 17 | 2034-2037 | |
| 41 | Conner Hurst | 17 | 2011-2014 | |
| 41 | Arturo Jiménez | 17 | 2013-2015 | |
| 41 | Michael Ladner | 17 | 2011-2014 | |
| 41 | Bill Lewis | 17 | 2007-2010 | |
| 41 | Ángel Luján | 17 | 2008-2011 | |
| 41 | Jeremy Perry# | 17 | 2028-2031 | |
| 41 | Katsunan Sato | 17 | 2011-2014 | |
| 41 | Gerardo Soto | 17 | 2010-2013 | |
| 41 | Shane Wallace# | 17 | 2034-2037 | |
| 41 | Lou Wilson | 17 | 2018-2021 | |
| 59 | Dan Boorman | 16 | 2015-2018 | |
| 59 | Norbert Bowling# | 16 | 2034-2037 | |
| 59 | Matt Brown# | 16 | 2018-2021 | |
| 59 | Charlie Caine# | 16 | 2036-2039 | |
| 59 | Lou Drewery# | 16 | 2025-2028 | |
| 59 | Hoyt Gardner | 16 | 2010-2013 | |
| 59 | Oliver González | 16 | 2009-2012 | |
| 59 | Woody Hetherington# | 16 | 2033-2036 | |
| 59 | Javier Jiménez | 16 | 2012-2015 | |
| 59 | Elton Kitchens# | 16 | 2034-2037 | |
| 59 | Donald Lesher# | 16 | 2020-2023 | |
| 59 | Jonathan Mason# | 16 | 2034-2037 | |
| 59 | Joe Matthews# | 16 | 2038-2040 | |
| 59 | Micheal McShane# | 16 | 2034-2037 | |
| 59 | Jason Meléndez# | 16 | 2026-2029 | |
| 59 | Chad Miller | 16 | 2011-2014 | |
| 59 | Bernardo Moreno | 16 | 2012-2015 | |
| 59 | Michael Reyes# | 16 | 2037-2040 | |
| 59 | Vernon Sullivan | 16 | 2008-2010 | |
| 59 | Glenn Taylor# | 16 | 2031-2034 | |
| 59 | Armando Vázquez | 16 | 2013-2015 | |
| 59 | Tom Welsh# | 16 | 2028-2031 | |
| 59 | Austin Williams | 16 | 2010-2013 | |
| 82 | Charles Austin | 15 | 2007-2010 | |
| 82 | Dave Baker# | 15 | 2037-2040 | |
| 82 | Pat Barr# | 15 | 2034-2037 | |
| 82 | Justin Barton | 15 | 2007-2010 | |
| 82 | Greg Bates# | 15 | 2026-2029 | |
| 82 | Millard Clark# | 15 | 2034-2037 | |
| 82 | Héctor Cortéz# | 15 | 2037-2040 | |
| 82 | Henry Dollman# | 15 | 2037-2040 | |
| 82 | Enrique Fonseca | 15 | 2010-2013 | |
| 82 | Curtis Fraser | 15 | 2015-2018 | |
| 82 | Christian George | 15 | 2010-2013 | |
| 82 | Jason Gould | 15 | 2009-2012 | |
| 82 | Fred Gross# | 15 | 2028-2031 | |
| 82 | Johnathan Hurlburt | 15 | 2020-2023 | |
| 82 | Mugombe Issa | 15 | 2012-2015 | |
| 82 | Benedict Kimball# | 15 | 2036-2039 | |
| 82 | George Ladd# | 15 | 2020-2023 | |
| 82 | Nick Lutz# | 15 | 2034-2037 | |
| 82 | Félix Maese | 15 | 2007-2010 |
