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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 | Joe Matthews# | 20 | 2038-2041 | |
| 17 | Matt Moody | 20 | 2010-2013 | |
| 20 | Jorge Castillo# | 19 | 2019-2022 | |
| 20 | Joshua Hall | 19 | 2015-2018 | |
| 20 | Michael Johnson | 19 | 2011-2014 | |
| 20 | Marvin Moore | 19 | 2020-2023 | |
| 20 | Paul Norris | 19 | 2013-2016 | |
| 20 | Otis Pearson | 19 | 2016-2019 | |
| 20 | Larry Schultz | 19 | 2009-2012 | |
| 20 | Shoichi Shimizu | 19 | 2011-2014 | |
| 20 | Kevin Thomas | 19 | 2020-2022 | |
| 20 | Ron Wilson# | 19 | 2019-2022 | |
| 30 | Kenny Ashley | 18 | 2011-2014 | |
| 30 | Víctor Carrillo | 18 | 2011-2014 | |
| 30 | Abel Castellanos# | 18 | 2036-2039 | |
| 30 | Walter Daniel | 18 | 2017-2020 | |
| 30 | Eric Grimes# | 18 | 2034-2037 | |
| 30 | Ben Holman# | 18 | 2025-2028 | |
| 30 | Max Jordan | 18 | 2010-2013 | |
| 30 | Jhong-shun Kong | 18 | 2010-2013 | |
| 30 | Mike Martínez# | 18 | 2036-2039 | |
| 30 | Adrián Navarro | 18 | 2014-2017 | |
| 30 | Mike Randall | 18 | 2019-2022 | |
| 30 | Daniel Sharpe | 18 | 2014-2017 | |
| 42 | Phil Anderson | 17 | 2008-2011 | |
| 42 | Christian Barrett# | 17 | 2034-2037 | |
| 42 | Allen Cook | 17 | 2018-2021 | |
| 42 | Salvador Delozada# | 17 | 2033-2036 | |
| 42 | Ben Ferguson# | 17 | 2036-2039 | |
| 42 | Alberto Flores# | 17 | 2025-2028 | |
| 42 | León Gil | 17 | 2018-2021 | |
| 42 | Christian Hardin# | 17 | 2034-2037 | |
| 42 | Conner Hurst | 17 | 2011-2014 | |
| 42 | Arturo Jiménez | 17 | 2013-2015 | |
| 42 | Samuel Johnston# | 17 | 2038-2041 | |
| 42 | Michael Ladner | 17 | 2011-2014 | |
| 42 | Bill Lewis | 17 | 2007-2010 | |
| 42 | Ángel Luján | 17 | 2008-2011 | |
| 42 | Jeremy Perry | 17 | 2028-2031 | |
| 42 | Katsunan Sato | 17 | 2011-2014 | |
| 42 | Gerardo Soto | 17 | 2010-2013 | |
| 42 | Shane Wallace# | 17 | 2034-2037 | |
| 42 | Lou Wilson | 17 | 2018-2021 | |
| 61 | Dan Boorman | 16 | 2015-2018 | |
| 61 | Norbert Bowling# | 16 | 2034-2037 | |
| 61 | Matt Brown | 16 | 2018-2021 | |
| 61 | Charlie Caine# | 16 | 2036-2039 | |
| 61 | Lou Drewery# | 16 | 2025-2028 | |
| 61 | Hoyt Gardner | 16 | 2010-2013 | |
| 61 | Ron Garrett# | 16 | 2038-2041 | |
| 61 | Oliver González | 16 | 2009-2012 | |
| 61 | Woody Hetherington# | 16 | 2033-2036 | |
| 61 | Javier Jiménez | 16 | 2012-2015 | |
| 61 | Elton Kitchens# | 16 | 2034-2037 | |
| 61 | Donald Lesher | 16 | 2020-2023 | |
| 61 | Jonathan Mason# | 16 | 2034-2037 | |
| 61 | Micheal McShane# | 16 | 2034-2037 | |
| 61 | Jason Meléndez# | 16 | 2026-2029 | |
| 61 | Chad Miller | 16 | 2011-2014 | |
| 61 | Bernardo Moreno | 16 | 2012-2015 | |
| 61 | Michael Reyes# | 16 | 2037-2040 | |
| 61 | Vernon Sullivan | 16 | 2008-2010 | |
| 61 | Glenn Taylor# | 16 | 2031-2034 | |
| 61 | Armando Vázquez | 16 | 2013-2015 | |
| 61 | Tom Welsh# | 16 | 2028-2031 | |
| 61 | Austin Williams | 16 | 2010-2013 | |
| 84 | Charles Austin | 15 | 2007-2010 | |
| 84 | Dave Baker# | 15 | 2037-2040 | |
| 84 | Pat Barr# | 15 | 2034-2037 | |
| 84 | Justin Barton | 15 | 2007-2010 | |
| 84 | Greg Bates# | 15 | 2026-2029 | |
| 84 | Ed Baxter# | 15 | 2038-2041 | |
| 84 | Henry Brown# | 15 | 2039-2042 | |
| 84 | Millard Clark# | 15 | 2034-2037 | |
| 84 | Héctor Cortéz# | 15 | 2037-2040 | |
| 84 | Henry Dollman# | 15 | 2037-2040 | |
| 84 | Enrique Fonseca | 15 | 2010-2013 | |
| 84 | Curtis Fraser | 15 | 2015-2018 | |
| 84 | Christian George | 15 | 2010-2013 | |
| 84 | Jason Gould | 15 | 2009-2012 | |
| 84 | Fred Gross# | 15 | 2028-2031 | |
| 84 | Johnathan Hurlburt | 15 | 2020-2023 | |
| 84 | Mugombe Issa | 15 | 2012-2015 |
