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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Lou Whitehead | 124 | 2002-2016 | |
| 2 | Elwood Bruce | 116 | 2062-2076 | |
| 3 | Ken Palmer | 109 | 1990-2000 | |
| 3 | Dino Talenti | 109 | 2039-2052 | |
| 5 | Salvador Gutierrez | 102 | 2062-2074 | |
| 5 | Miguel Hurtado | 102 | 2056-2073 | |
| 7 | Luis Delgado | 101 | 2020-2034 | |
| 7 | Roman Mathias | 101 | 2025-2036 | |
| 7 | Tim Moore | 101 | 1999-2012 | |
| 10 | Francisco Marés | 99 | 1994-2004 | |
| 10 | Ramón Ramírez | 99 | 1995-2007 | |
| 12 | Dennis Hartman | 98 | 2050-2064 | |
| 13 | Enrique Colón | 96 | 2028-2035 | |
| 13 | Robert Dorsey | 96 | 2012-2019 | |
| 15 | Joel Curtis | 95 | 1993-2004 | |
| 15 | Eduardo Romano | 95 | 2059-2070 | |
| 15 | Bartolo Téllez | 95 | 2020-2030 | |
| 18 | Duane Moore | 94 | 1993-2006 | |
| 18 | Seth Slade | 94 | 2029-2044 | |
| 20 | José Aguirre | 93 | 1992-2001 | |
| 20 | Jorge Blanco | 93 | 2032-2045 | |
| 22 | Danny Hill | 92 | 2062-2076 | |
| 22 | Franky Santegoeds | 92 | 2053-2065 | |
| 24 | Hwui-ning Ling | 88 | 2001-2014 | |
| 25 | Gerald Noordam | 86 | 2052-2067 | |
| 26 | Warner Cavanagh | 85 | 2044-2062 | |
| 26 | Craig Walker | 85 | 1991-1999 | |
| 28 | Thomas Barrett | 84 | 2009-2018 | |
| 28 | Leonard Clark | 84 | 1993-2006 | |
| 28 | Jared Kozlowski | 84 | 2055-2068 | |
| 31 | Les Saunders | 83 | 1990-1998 | |
| 31 | Jared Small | 83 | 2040-2050 | |
| 33 | Brandon Benoit | 82 | 2035-2051 | |
| 33 | Julian Phillips | 82 | 2004-2014 | |
| 35 | Larry Daig | 81 | 2065-2076 | |
| 36 | Vaughn Gibson | 79 | 1997-2007 | |
| 36 | Don Pretty# | 79 | 2066-2081 | |
| 36 | Hiroshige Uchida | 79 | 2000-2018 | |
| 36 | Christopher Wicks | 79 | 1997-2007 | |
| 40 | Ludovic Buttone | 78 | 2020-2030 | |
| 40 | Vern Garbie | 78 | 2061-2075 | |
| 40 | Josh Gesler | 78 | 2044-2057 | |
| 40 | Gianfranco Lamborghini | 78 | 2024-2039 | |
| 40 | Ossie Lopez | 78 | 2068-2080 | |
| 45 | Naruhiko Abe | 77 | 2028-2039 | |
| 45 | Todd Graves | 77 | 1998-2007 | |
| 45 | Tony Webber | 77 | 2061-2071 | |
| 45 | Arthur Woodruff | 77 | 2034-2046 | |
| 49 | António Alvarado | 76 | 1990-1996 | |
| 49 | Julian Braber | 76 | 2034-2050 | |
| 49 | Mitsuhiro Nishimura | 76 | 2059-2068 | |
| 49 | Steve Owen | 76 | 2033-2041 | |
| 49 | Ramón Rivas | 76 | 2003-2014 | |
| 49 | Eric Wright | 76 | 2024-2033 | |
| 55 | Bill Carr | 75 | 2037-2047 | |
| 55 | Vincente González | 75 | 2024-2035 | |
| 57 | Fernando Gomez# | 74 | 2070-2081 | |
| 57 | Matsuo Ikarashi | 74 | 2030-2038 | |
| 57 | Mike Parsons | 74 | 2031-2038 | |
| 57 | Ed Powell | 74 | 2055-2067 | |
| 57 | Javier Rivera | 74 | 1996-2006 | |
| 62 | Gerald Sullivan | 73 | 2024-2033 | |
| 63 | Paul Mercer | 72 | 2042-2051 | |
| 63 | Ryan Moore | 72 | 2024-2036 | |
| 63 | Ken Ramsay | 72 | 2034-2046 | |
| 66 | Stu Caron | 71 | 2028-2041 | |
| 66 | Joe Coffman | 71 | 2000-2017 | |
| 66 | Alex Henderson | 71 | 2023-2037 | |
| 66 | Aaron Lawson | 71 | 1993-1999 | |
| 66 | George McGee | 71 | 2022-2040 | |
| 66 | Dave Peterson | 71 | 1998-2007 | |
| 72 | Aaron Carter | 70 | 2011-2021 | |
| 72 | Jorge Herrera | 70 | 1995-2002 | |
| 72 | Joe Larson | 70 | 2039-2051 | |
| 72 | Claudio Lópes | 70 | 1991-2002 | |
| 72 | Luis Marulnda | 70 | 1990-2000 | |
| 72 | Dan Winston | 70 | 2013-2026 | |
| 78 | José Chávez | 69 | 1994-2001 | |
| 78 | Norbert Kooiman | 69 | 2024-2036 | |
| 78 | Chris Lambert | 69 | 1996-2010 | |
| 78 | George Lloyd | 69 | 2032-2047 | |
| 78 | Bartolomeo Masini | 69 | 2053-2063 | |
| 78 | Juan Núñez | 69 | 2000-2007 | |
| 78 | Jorge Ochoa | 69 | 2017-2023 | |
| 78 | Neville Roosemont | 69 | 2053-2067 | |
| 78 | Sam Sullivan | 69 | 2034-2043 | |
| 78 | Miguel Vásquez | 69 | 2005-2018 | |
| 78 | Tom Webber | 69 | 2004-2014 | |
| 78 | Pat Young | 69 | 1997-2007 | |
| 90 | Francisco Hernández | 68 | 2046-2056 | |
| 90 | Mike Horton | 68 | 2000-2009 | |
| 90 | Marlon James | 68 | 1990-1998 | |
| 90 | Steve McPhee | 68 | 2072-2078 | |
| 90 | Victor Pire | 68 | 2059-2072 | |
| 90 | Folkert Scherpenisse | 68 | 2061-2070 | |
| 96 | Ernie Christian | 67 | 1990-2004 | |
| 96 | Mike Freeman | 67 | 2056-2071 | |
| 96 | Teodor Reyes | 67 | 1999-2008 | |
| 96 | Henry Williams | 67 | 2036-2042 | |
| 100 | Simon-Pierre Gagnon | 66 | 2056-2069 |
