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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | B.J. Heimbach | 56 | 2036-2040 | |
| 2 | Mike Williams | 48 | 2028-2031 | |
| 3 | Tate Lloret# | 44 | 2045-2048 | |
| 4 | Kai Bell | 43 | 2030-2033 | |
| 4 | Luis Mora | 43 | 2004-2008 | |
| 6 | C.J. Butler | 41 | 2011-2015 | |
| 6 | Eric Carr | 41 | 2012-2015 | |
| 6 | Romeo Castañeda | 41 | 2036-2042 | |
| 6 | Oscar Miranda | 41 | 2026-2027 | |
| 10 | Bobby Brady | 40 | 2030-2034 | |
| 11 | Mike Gustafson | 39 | 2017-2021 | |
| 11 | Nout Noordervliet | 39 | 2035-2040 | |
| 13 | Miguel Munoz | 38 | 2009-2012 | |
| 13 | Rob Proffer | 38 | 2018-2023 | |
| 15 | Scott Bates | 37 | 2009-2015 | |
| 15 | Dusty Dowdle | 37 | 2016-2018 | |
| 15 | Bobby Link | 37 | 2006-2009 | |
| 15 | Jorge Morales | 37 | 2004-2007 | |
| 15 | Sandy Rascon | 37 | 2024-2027 | |
| 15 | Adam Westgard | 37 | 2025-2028 | |
| 15 | Ricardo Winter | 37 | 2032-2036 | |
| 22 | Terrance Chisolm | 36 | 2045-2047 | |
| 22 | Steadman Page | 36 | 2045-2047 | |
| 22 | Bill Rosales | 36 | 2028-2033 | |
| 22 | Derril Schunemann | 36 | 2031-2033 | |
| 22 | Sam Seligmann | 36 | 2026-2031 | |
| 22 | Josh Sherman | 36 | 2017-2021 | |
| 22 | Rob Toonen | 36 | 2005-2009 | |
| 29 | Sean Bay | 35 | 2016-2018 | |
| 29 | Mike Pederson | 35 | 2022-2024 | |
| 29 | Ryan Pinkerman | 35 | 2010-2012 | |
| 29 | Ryan Starr | 35 | 2012-2016 | |
| 29 | Jagger Tucker | 35 | 2035-2039 | |
| 29 | T.J. Villalon | 35 | 2030-2034 | |
| 35 | Rich Oyola | 34 | 2031-2035 | |
| 35 | Gerardo Solis | 34 | 2008-2012 | |
| 37 | Juan Casamayor | 33 | 2004-2009 | |
| 37 | Elijah Lee | 33 | 2044-2047 | |
| 37 | Cody Pennington | 33 | 2010-2015 | |
| 37 | Danny Valdez | 33 | 2022-2023 | |
| 37 | Eytor Vasques | 33 | 2004-2008 | |
| 37 | Matt Weaver | 33 | 2029-2031 | |
| 43 | Julián Cáceres# | 32 | 2046-2050 | |
| 43 | Diego Heredia | 32 | 2039-2041 | |
| 43 | Curt Hughes | 32 | 2028-2030 | |
| 43 | Santiago Manzanaros# | 32 | 2045-2049 | |
| 43 | Francisco Nieves | 32 | 2020-2024 | |
| 43 | Jonathan Thomas# | 32 | 2040-2042 | |
| 49 | Manny Barron | 31 | 2013-2017 | |
| 49 | Zach Bevington | 31 | 2014-2017 | |
| 49 | Jim Boothe | 31 | 2014-2018 | |
| 49 | Omar Casso | 31 | 2012-2016 | |
| 49 | Alexis Castaneda | 31 | 2023-2029 | |
| 49 | Dean Clapp# | 31 | 2048-2049 | |
| 49 | Alfredo Degorrio | 31 | 2008-2012 | |
| 49 | Nick Farr | 31 | 2016-2022 | |
| 49 | Oliver Juarez | 31 | 2014-2019 | |
| 49 | Shepherd Lacroix# | 31 | 2039-2042 | |
| 49 | Bobby Martinez | 31 | 2019-2022 | |
| 49 | Gabriel Nova# | 31 | 2042-2044 | |
| 49 | Kyle Oberlin | 31 | 2034-2038 | |
| 49 | Corey Patton | 31 | 2014-2016 | |
| 49 | Adrian Paul | 31 | 2038-2040 | |
| 49 | Nick Torley | 31 | 2009-2013 | |
| 49 | Danny Velez | 31 | 2014-2019 | |
| 66 | Kymani Armwood | 30 | 2004-2007 | |
| 66 | Luis Bastidas | 30 | 2004-2006 | |
| 66 | Orlando Burgos | 30 | 2020-2023 | |
| 66 | Damon Castillo | 30 | 2030-2032 | |
| 66 | Jeronimo Cedeño | 30 | 2035-2037 | |
| 66 | Nathaniel Duff | 30 | 2036-2038 | |
| 66 | Joe Fulmer | 30 | 2017-2019 | |
| 66 | Steve Glazewski | 30 | 2034-2036 | |
| 66 | Jonatan Herrera | 30 | 2032-2034 | |
| 66 | Wyatt Magnifico | 30 | 2044-2049 | |
| 66 | Aznaro Mejia# | 30 | 2047-2049 | |
| 66 | Frank Molnar# | 30 | 2048-2050 | |
| 78 | Carlos Alanis | 29 | 2030-2033 | |
| 78 | Justin Amand | 29 | 2020-2022 | |
| 78 | Francisco Aragon | 29 | 2019-2021 | |
| 78 | Gill Fernández | 29 | 2040-2043 | |
| 78 | Tomasi Finau | 29 | 2037-2040 | |
| 78 | Jahiem Gaiters | 29 | 2005-2010 | |
| 78 | Kevin Glenn | 29 | 2026-2028 | |
| 78 | Henry Jaimes | 29 | 2029-2030 | |
| 78 | Danny Lazzari | 29 | 2016-2020 | |
| 78 | Danny Marte | 29 | 2014-2016 | |
| 78 | Tony Miranda | 29 | 2026-2029 | |
| 78 | Marcos Montenegro | 29 | 2018-2019 | |
| 78 | Jon Montoya | 29 | 2010-2014 | |
| 78 | Chad Norris | 29 | 2007-2010 | |
| 78 | Alvaro Razo | 29 | 2035-2037 | |
| 78 | Joe Reyes | 29 | 2012-2015 | |
| 78 | Alfredo Tavarez | 29 | 2024-2026 | |
| 78 | Dennis Webb | 29 | 2016-2018 | |
| 96 | Luis Avalos | 28 | 2008-2012 | |
| 96 | Zach Barnett | 28 | 2029-2032 | |
| 96 | Charlie Beal | 28 | 2035-2039 | |
| 96 | Stan Betancourt# | 28 | 2040-2042 | |
| 96 | Jeff Bond | 28 | 2025-2026 |
