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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Lee Dailey | 177 | 1957-1967 | |
| 2 | Dave Beadle | 164 | 1960-1969 | |
| 3 | Tony Lowe | 163 | 1968-1981 | |
| 4 | Pablo Lugo | 143 | 1991-2005 | |
| 5 | John Bang | 134 | 1959-1968 | |
| 6 | Sean Ward | 131 | 1967-1975 | |
| 7 | Edgar Geil | 129 | 1957-1969 | |
| 8 | William Piscitelli | 128 | 1957-1970 | |
| 9 | Michael Wood | 127 | 1957-1965 | |
| 10 | Terry Laing | 124 | 1957-1966 | |
| 11 | Stephen Hollins | 123 | 1960-1969 | |
| 12 | Victor Barnes | 121 | 1958-1968 | |
| 13 | Frank LeBlanc | 118 | 1967-1983 | |
| 14 | Seth Allen | 117 | 1957-1968 | |
| 15 | Ron Oliver | 115 | 1964-1975 | |
| 16 | Jesús Romero | 114 | 1981-1989 | |
| 17 | Richard Mayor | 113 | 1957-1969 | |
| 18 | Shannon Bowie | 112 | 1957-1968 | |
| 19 | Nelson Padilla | 109 | 1999-2014 | |
| 19 | Bill Price# | 109 | 2003-2014 | |
| 19 | Arturo Vázquez# | 109 | 2002-2014 | |
| 22 | Ed Curran# | 107 | 2002-2014 | |
| 22 | Sergio Maldonado | 107 | 1962-1975 | |
| 22 | Robbie Moore | 107 | 1970-1983 | |
| 25 | Jon Frierson | 106 | 1959-1970 | |
| 25 | Roy Mann | 106 | 1964-1977 | |
| 27 | Larry Hines | 105 | 1982-1995 | |
| 28 | Jason Moore | 104 | 1962-1973 | |
| 29 | Scott Antonio | 101 | 1996-2010 | |
| 29 | Bill Mitchell | 101 | 1966-1977 | |
| 31 | Pablo Águila | 100 | 1992-2004 | |
| 32 | António Násquez | 99 | 1994-2006 | |
| 32 | Jim Thompson | 99 | 1964-1975 | |
| 34 | Thomas Clayton | 98 | 1975-1983 | |
| 35 | Phil Longchamps# | 97 | 2005-2014 | |
| 35 | Ben Moore | 97 | 1974-1981 | |
| 37 | Chester Bailey | 95 | 1972-1986 | |
| 37 | Hidehira Ikarashi | 95 | 1967-1980 | |
| 37 | Bennett Owens | 95 | 1975-1985 | |
| 40 | Orlando Briceno | 93 | 1958-1963 | |
| 40 | David Schneider | 93 | 1962-1972 | |
| 42 | Herman Conway | 92 | 1957-1969 | |
| 42 | Santiago Gómez | 92 | 1966-1979 | |
| 42 | Júlio Rocha# | 92 | 2001-2014 | |
| 45 | António González | 91 | 1971-1984 | |
| 45 | Randy Laidlaw | 91 | 1988-2000 | |
| 45 | John Rogers | 91 | 1957-1965 | |
| 45 | Alberto Ruíz | 91 | 1969-1975 | |
| 49 | Ray Hawkins | 90 | 1991-2001 | |
| 49 | Terence Washington | 90 | 1988-2000 | |
| 51 | Carlos De Jesús | 89 | 1968-1979 | |
| 51 | Roger Francis# | 89 | 2004-2014 | |
| 51 | José Rodríguez | 89 | 1993-2008 | |
| 51 | Tim Ward | 89 | 1970-1981 | |
| 55 | Lynn Alexander | 88 | 1966-1976 | |
| 55 | Allen Brady | 88 | 1962-1972 | |
| 55 | José Esparza# | 88 | 2006-2014 | |
| 55 | Sergio Martínez | 88 | 1974-1981 | |
| 59 | Michael Ballard | 87 | 1968-1976 | |
| 59 | John Johnson | 87 | 1969-1976 | |
| 59 | Delbert Talarico | 87 | 1957-1966 | |
| 62 | Richard Barr | 86 | 1962-1969 | |
| 62 | John Crow | 86 | 1983-1992 | |
| 62 | Randy De Jesús | 86 | 1993-2005 | |
| 62 | Eric Kemp | 86 | 1969-1978 | |
| 66 | Brad Brooks | 85 | 1999-2009 | |
| 66 | Carlos Camacho# | 85 | 2000-2014 | |
| 66 | Bill Forester | 85 | 1957-1965 | |
| 66 | Marvin Glenn | 85 | 1967-1977 | |
| 66 | Mark Gregg | 85 | 1998-2010 | |
| 71 | Thomas Chee | 84 | 1957-1962 | |
| 71 | Jose Cruz | 84 | 1958-1969 | |
| 71 | Martin Martínez | 84 | 1993-2000 | |
| 71 | Toby Nix | 84 | 1983-1992 | |
| 71 | Donald Wright | 84 | 1957-1962 | |
| 71 | Rodrigo Ávila | 84 | 2000-2008 | |
| 77 | António Gallardo | 83 | 1996-2009 | |
| 77 | Pepe Ramírez | 83 | 1964-1969 | |
| 77 | Robbie Stuart | 83 | 1987-1995 | |
| 80 | Richard Blevins | 82 | 1965-1975 | |
| 80 | José Castro | 82 | 1968-1973 | |
| 80 | Donato Gil | 82 | 1993-2007 | |
| 80 | Christian Piper | 82 | 1998-2007 | |
| 80 | Roberto Vázquez | 82 | 1989-2002 | |
| 85 | Sean Connolly | 81 | 1988-2000 | |
| 85 | José Valéncia | 81 | 1990-1998 | |
| 87 | Murray Gallagher | 80 | 1993-2004 | |
| 87 | Edgar Vásquez# | 80 | 2006-2014 | |
| 87 | Kumanosuke Yamashita | 80 | 1966-1979 | |
| 90 | Esteban Aguirre | 79 | 1995-2008 | |
| 90 | James Ayers | 79 | 1957-1962 | |
| 90 | Kelly Kirkland | 79 | 1972-1981 | |
| 90 | Jason Mann | 79 | 1979-1987 | |
| 94 | Jesús Cardenas# | 78 | 2005-2014 | |
| 94 | Jeff Cook | 78 | 1989-2005 | |
| 94 | Paco Flores | 78 | 1992-2003 | |
| 94 | Rob Johnston | 78 | 1971-1975 | |
| 94 | Keith Kimbell | 78 | 1957-1961 | |
| 94 | Chase Sharper | 78 | 1957-1964 | |
| 94 | Timothy Stradford | 78 | 1957-1968 |
