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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Aurelio Morales# | 81 | 2025-2031 | |
| 2 | António Alonzo | 68 | 2010-2023 | |
| 3 | Lee Ollis# | 65 | 2023-2028 | |
| 4 | José Gutiérrez# | 61 | 2025-2031 | |
| 5 | Nick Davis | 59 | 2006-2015 | |
| 6 | Eric Budo# | 57 | 2022-2028 | |
| 6 | Rupert Hunt# | 57 | 2026-2031 | |
| 8 | Chad Durbin | 55 | 1999-2008 | |
| 9 | Glenn Brown | 54 | 2008-2015 | |
| 9 | Burl Kelley | 54 | 2008-2011 | |
| 11 | Tony Ramírez | 53 | 2002-2008 | |
| 12 | Mark Clark | 52 | 1991-2001 | |
| 13 | Bob Águila# | 51 | 2027-2031 | |
| 14 | Homer Bailey | 50 | 2010-2019 | |
| 14 | Trevor Foster | 50 | 2016-2023 | |
| 16 | Jeffrey Schofield# | 49 | 2027-2031 | |
| 16 | Jason Willis | 49 | 2008-2011 | |
| 18 | José Féliz | 48 | 2009-2021 | |
| 18 | Jeremy Parker# | 48 | 2026-2031 | |
| 18 | Rob Patterson | 48 | 2000-2008 | |
| 18 | Dan Rasmussen | 48 | 2007-2016 | |
| 22 | John Anderson | 47 | 2008-2018 | |
| 22 | Jerry Bailey | 47 | 2002-2008 | |
| 22 | Mathew Quick | 47 | 2000-2007 | |
| 22 | Leonardo Rodríguez | 47 | 2000-2008 | |
| 26 | Bob Foreman | 45 | 2009-2020 | |
| 26 | Jordan Fuller# | 45 | 2027-2031 | |
| 28 | Armando Galarraga | 44 | 2009-2022 | |
| 28 | Vicente García | 44 | 2002-2013 | |
| 28 | Kyle Lynch | 44 | 2010-2017 | |
| 31 | Tom Kane | 43 | 2008-2015 | |
| 31 | Mark King | 43 | 2016-2018 | |
| 33 | Bill Beck# | 42 | 2024-2029 | |
| 33 | Roberto Leal | 42 | 2008-2021 | |
| 33 | Dan Middleton | 42 | 2007-2012 | |
| 36 | Orlando Herrera# | 41 | 2025-2030 | |
| 36 | Jong-bum Hong# | 41 | 2026-2031 | |
| 36 | Kyle McClellan | 41 | 2010-2022 | |
| 36 | John Roper | 41 | 1993-2005 | |
| 40 | Archie Anderson | 40 | 2004-2015 | |
| 40 | Sidney Ponson | 40 | 1998-2001 | |
| 40 | Manuel Trevino# | 40 | 2023-2031 | |
| 40 | Francisco Valéncia | 40 | 2013-2023 | |
| 44 | Sidney Awdry# | 39 | 2028-2031 | |
| 44 | Tom Barlow# | 39 | 2024-2027 | |
| 44 | Russell Bird | 39 | 2001-2014 | |
| 44 | Bob Callbeck# | 39 | 2025-2029 | |
| 44 | Xavier Fallon | 39 | 2010-2012 | |
| 44 | Les Huggins | 39 | 2008-2012 | |
| 44 | Todd Manning | 39 | 2006-2015 | |
| 44 | Eric Sears# | 39 | 2022-2028 | |
| 52 | Andy Cameron | 38 | 2006-2017 | |
| 52 | Víctor Dueñas# | 38 | 2018-2022 | |
| 52 | Terry Duffy | 38 | 2008-2019 | |
| 52 | Mike Jordan | 38 | 2002-2013 | |
| 52 | Paul Williams | 38 | 2009-2011 | |
| 57 | Joe Moore | 37 | 2016-2018 | |
| 57 | Emílio Márquez# | 37 | 2027-2031 | |
| 57 | Michael Pineda | 37 | 2009-2014 | |
| 57 | Juan Vargas# | 37 | 2027-2030 | |
| 61 | Alejandro Bruno# | 36 | 2027-2031 | |
| 61 | Gilberto Gómez# | 36 | 2024-2031 | |
| 61 | Jason Johnson | 36 | 1997-2006 | |
| 61 | Tommy Johnson | 36 | 2016-2023 | |
| 61 | John Lannan | 36 | 2008-2011 | |
| 61 | Mal Moore# | 36 | 2023-2029 | |
| 61 | Cole Reeves | 36 | 2019-2023 | |
| 61 | Brad Ziegler | 36 | 2009-2022 | |
| 69 | Bob Anderson | 35 | 2009-2022 | |
| 69 | Keith Bell | 35 | 2000-2005 | |
| 69 | Mike Campbell | 35 | 2006-2008 | |
| 69 | Rocky Coppinger | 35 | 1996-2004 | |
| 69 | Frank Green | 35 | 2002-2016 | |
| 69 | Casey Janssen | 35 | 2011-2015 | |
| 69 | Enrico Rúbio# | 35 | 2023-2028 | |
| 76 | David Bush | 34 | 2004-2017 | |
| 76 | Joba Chamberlain | 34 | 2010-2011 | |
| 76 | Ubaldo Jimenez | 34 | 2007-2018 | |
| 76 | Alexander Martin | 34 | 2009-2018 | |
| 76 | Roy McKinney | 34 | 2007-2020 | |
| 76 | Michael Payne | 34 | 2017-2023 | |
| 76 | Mark Yates# | 34 | 2025-2031 | |
| 76 | Sung-tae Yi# | 34 | 2025-2030 | |
| 76 | Jason Yoder | 34 | 2013-2016 | |
| 76 | Robert Zavala# | 34 | 2026-2029 | |
| 86 | Alberto Cervantes# | 33 | 2025-2030 | |
| 86 | Robert Dixon# | 33 | 2017-2019 | |
| 86 | Scott Eyre | 33 | 1997-2004 | |
| 86 | Aaron Goodman | 33 | 2003-2004 | |
| 86 | Forrest Jackson# | 33 | 2024-2031 | |
| 86 | Rob Johnston# | 33 | 2022-2024 | |
| 86 | Bob Parker | 33 | 2016-2022 | |
| 86 | Will Urry# | 33 | 2020-2027 | |
| 94 | Joaquin Benoit | 32 | 2003-2011 | |
| 94 | Jamie Brown | 32 | 2007-2018 | |
| 94 | Nick Fisher | 32 | 2010-2019 | |
| 94 | Javier García | 32 | 2010-2023 | |
| 94 | Haywood Horn | 32 | 2002-2005 | |
| 94 | Matt Hortez# | 32 | 2028-2031 | |
| 94 | Phil Hughes | 32 | 2010-2016 |
