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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Manuel Hernández | 58 | 1970-1976 | |
| 2 | Brandon Moody | 56 | 1976-1981 | |
| 3 | Reggie Davies | 55 | 1986-1991 | |
| 4 | Santiago Raymos | 51 | 1986-1991 | |
| 5 | Johnny Hudson | 50 | 1972-1977 | |
| 5 | Andrew Norman | 50 | 1979-1983 | |
| 7 | Iván Arévalo | 48 | 1999-2003 | |
| 7 | Bob Perry | 48 | 1994-1998 | |
| 7 | Jonathan Walls | 48 | 1993-1999 | |
| 10 | Juan Jose Colón | 46 | 1970-1976 | |
| 10 | José Guzmán | 46 | 1986-1991 | |
| 10 | Francisco Jiménez | 46 | 1983-1985 | |
| 10 | Norm O'Quinn | 46 | 1970-1976 | |
| 10 | Miguel Varela | 46 | 1993-1998 | |
| 15 | Rafael Hinojosa | 45 | 1974-1976 | |
| 16 | Luis Pérez | 44 | 1983-1988 | |
| 17 | Ken Burris | 43 | 1983-1987 | |
| 17 | John Rice | 43 | 1970-1976 | |
| 17 | Ron Seals | 43 | 1973-1976 | |
| 20 | Brian Fritz | 42 | 1986-1989 | |
| 21 | Alfredo Flores | 41 | 1988-1994 | |
| 21 | Clement Jones | 41 | 1974-1977 | |
| 21 | Austin Morrison | 41 | 1983-1985 | |
| 21 | José Soto | 41 | 1975-1978 | |
| 21 | Juan Vásquez | 41 | 1983-1986 | |
| 26 | Cisco Caro | 40 | 1983-1985 | |
| 26 | Gary Hooper | 40 | 1990-1994 | |
| 26 | Martin Jenkins | 40 | 1971-1976 | |
| 29 | Pat Bailey | 39 | 1970-1975 | |
| 29 | Flynn Berndt | 39 | 1970-1975 | |
| 29 | Lúcio Herrera | 39 | 2011-2015 | |
| 29 | Chris Hudson | 39 | 1981-1984 | |
| 29 | Jeremy Ludwick | 39 | 1976-1979 | |
| 29 | Melvin Miller | 39 | 1978-1982 | |
| 29 | Dallas Minor | 39 | 1979-1981 | |
| 29 | Keith Owens | 39 | 1980-1983 | |
| 29 | Eugene Payton | 39 | 1973-1977 | |
| 29 | Mike Smith | 39 | 1988-1992 | |
| 29 | Chad Staten | 39 | 1985-1989 | |
| 29 | Martin Walker | 39 | 1972-1977 | |
| 41 | Reggie Brantley | 38 | 2009-2016 | |
| 41 | Rhett Callender | 38 | 1981-1984 | |
| 41 | Justin Coker | 38 | 1988-1992 | |
| 41 | Rob DeWitt | 38 | 1970-1975 | |
| 41 | Ken Finley | 38 | 1984-1986 | |
| 41 | Mike Ford | 38 | 2008-2014 | |
| 41 | Greg Fox | 38 | 2002-2005 | |
| 41 | Vicente Mata | 38 | 1996-1999 | |
| 41 | A.R. Ober | 38 | 1995-1999 | |
| 41 | Juan Ventura | 38 | 1975-1977 | |
| 41 | Andre Woods | 38 | 1971-1975 | |
| 41 | Ronnie Yarbrough | 38 | 1999-2003 | |
| 53 | Arturo Herrera | 37 | 1972-1977 | |
| 53 | Luis Nieves | 37 | 1971-1974 | |
| 55 | Eric Baker | 36 | 2000-2008 | |
| 55 | Tony Carrillo | 36 | 1988-1993 | |
| 55 | Juan Carlos Cortéz | 36 | 1970-1976 | |
| 55 | Domingo Gámez | 36 | 2011-2017 | |
| 55 | Pepe Hernández | 36 | 1977-1980 | |
| 55 | Terry Martin | 36 | 1983-1988 | |
| 55 | Júlio Martínez | 36 | 1978-1981 | |
| 55 | Júlio Méndez | 36 | 1971-1976 | |
| 55 | Félix Montańo | 36 | 1970-1976 | |
| 55 | Vic O'Reilly | 36 | 1977-1979 | |
| 55 | Tony Rivera | 36 | 1982-1985 | |
| 55 | Terry Schneider | 36 | 1972-1977 | |
| 55 | Thomas Smith | 36 | 1983-1987 | |
| 55 | Paco Solano | 36 | 1972-1976 | |
| 55 | Chris Taylor | 36 | 1977-1981 | |
| 55 | Anthony Tolbert | 36 | 1986-1988 | |
| 55 | Tommy Welch | 36 | 1983-1985 | |
| 72 | Mike Blackburn | 35 | 1987-1992 | |
| 72 | Zak Brown | 35 | 1993-1996 | |
| 72 | Ryan Dunworth | 35 | 1972-1976 | |
| 72 | Bill Gray | 35 | 1995-1999 | |
| 72 | Mario Ortíz | 35 | 1986-1989 | |
| 72 | Andrew Williams | 35 | 1970-1975 | |
| 78 | José Alonzo | 34 | 1978-1982 | |
| 78 | Dennis Anderson | 34 | 1993-1997 | |
| 78 | Pedro Bustamante | 34 | 1970-1976 | |
| 78 | Lúcio Dávila | 34 | 1984-1987 | |
| 78 | Pablo García | 34 | 1981-1984 | |
| 78 | John Gilbert | 34 | 1972-1977 | |
| 78 | Jason Holbrook | 34 | 1983-1987 | |
| 78 | Glenn Hovey | 34 | 1986-1991 | |
| 78 | Paul Hutchins | 34 | 1971-1976 | |
| 78 | Ed Johnston | 34 | 1992-2000 | |
| 78 | Bob Lawson | 34 | 1984-1989 | |
| 78 | James McConnell | 34 | 1984-1988 | |
| 78 | Carlos Murgilla | 34 | 1982-1987 | |
| 78 | Chad Pfeifer | 34 | 1989-1992 | |
| 78 | Rob Powers | 34 | 1999-2001 | |
| 78 | Oliver Torres | 34 | 1972-1976 | |
| 78 | Rick Walsh | 34 | 1981-1984 | |
| 95 | Nathan Barker | 33 | 2010-2015 | |
| 95 | Armando Cabral | 33 | 1986-1991 | |
| 95 | Víctor Delgado | 33 | 1980-1985 | |
| 95 | Nate Jackson | 33 | 1983-1987 | |
| 95 | Trent Jones | 33 | 1983-1987 | |
| 95 | Jaime Morales | 33 | 1997-2001 |
