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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Joseph Rogers | 57 | 1982-1988 | |
| 2 | Larry LeJeune | 56 | 1970-1975 | |
| 3 | Alberto Cuellar | 48 | 1970-1975 | |
| 3 | Kenny Garland | 48 | 1977-1981 | |
| 5 | Artie Bailey | 46 | 1988-1994 | |
| 6 | Rich Long | 45 | 1978-1983 | |
| 6 | Jesús Rodríguez | 45 | 1985-1991 | |
| 8 | José Ojeda | 44 | 1992-1995 | |
| 9 | Elton Benson | 43 | 1977-1981 | |
| 9 | Peter Clarke | 43 | 1980-1984 | |
| 9 | Pedro Cortéz | 43 | 1974-1980 | |
| 9 | John Moody | 43 | 2009-2014 | |
| 9 | Ryan O'Toole | 43 | 1985-1987 | |
| 9 | José Pineda | 43 | 1977-1981 | |
| 9 | Mac Smart | 43 | 1974-1978 | |
| 16 | Trevor Bailey | 42 | 1977-1983 | |
| 16 | Brad Dunlap | 42 | 1973-1976 | |
| 16 | Randy Johnson | 42 | 2005-2012 | |
| 19 | Craig Chappell | 41 | 1985-1987 | |
| 19 | Fernando Flores | 41 | 1977-1982 | |
| 21 | Gabriel Hernández | 40 | 1970-1976 | |
| 21 | Ricardo Ocampo | 40 | 1984-1987 | |
| 21 | Gustavo Rivas | 40 | 1989-1993 | |
| 24 | Bobby Day | 39 | 1973-1976 | |
| 24 | John Henderson | 39 | 1988-1992 | |
| 24 | Allen King | 39 | 1975-1979 | |
| 24 | Gary Stafford | 39 | 2009-2011 | |
| 28 | Kirk Andrés | 38 | 2012-2017 | |
| 28 | Dave Daniels | 38 | 1984-1987 | |
| 28 | Doug Hatherall | 38 | 1977-1981 | |
| 28 | Luis Salinas | 38 | 1982-1987 | |
| 28 | Albert Torres | 38 | 1974-1976 | |
| 28 | Tony Wilkinson | 38 | 1981-1985 | |
| 28 | Jeff Wilson | 38 | 1985-1988 | |
| 35 | Ralph Adams | 37 | 1978-1981 | |
| 35 | Cy Anderson | 37 | 1988-1994 | |
| 35 | Armando Gutiérrez | 37 | 1970-1976 | |
| 35 | Billy Kendall | 37 | 1987-1991 | |
| 35 | Terry Lamb | 37 | 1977-1980 | |
| 35 | Eric Martell | 37 | 1995-1998 | |
| 35 | Máximo Ortíz | 37 | 1976-1980 | |
| 35 | António Rivera | 37 | 1988-1993 | |
| 35 | Will Urquhart | 37 | 1984-1987 | |
| 44 | Jimmy Cooper | 36 | 2007-2011 | |
| 44 | Luis Rodríguez | 36 | 1985-1991 | |
| 44 | José Vázquez | 36 | 1970-1974 | |
| 47 | Archie Chambers | 35 | 1987-1991 | |
| 47 | Matt Johnson | 35 | 1973-1979 | |
| 47 | Rich Larkin | 35 | 1997-2000 | |
| 47 | Aaron Spivey | 35 | 1970-1973 | |
| 47 | Raúl Valdés | 35 | 2006-2011 | |
| 52 | Trevor Bell | 34 | 1985-1987 | |
| 52 | Manny Cruz | 34 | 1993-1999 | |
| 52 | Rob DeWitt | 34 | 1971-1975 | |
| 52 | Michael Ferán | 34 | 1975-1979 | |
| 52 | John Nicholson | 34 | 1972-1974 | |
| 52 | Leo Russell | 34 | 1995-1999 | |
| 52 | Raúl Villalvir | 34 | 1971-1974 | |
| 52 | Henry Williams | 34 | 1984-1987 | |
| 60 | Randy Bailey | 33 | 1985-1991 | |
| 60 | José Costello | 33 | 1980-1984 | |
| 60 | Manuel Delgado | 33 | 1970-1975 | |
| 60 | Steve Murphy | 33 | 1995-2000 | |
| 60 | Reginald Neal | 33 | 1975-1980 | |
| 60 | Jason Pike | 33 | 1991-1995 | |
| 60 | Matt Thompson | 33 | 1972-1976 | |
| 67 | Barry Aldridge | 32 | 1986-1991 | |
| 67 | Matt Brock | 32 | 1984-1986 | |
| 67 | Kenny Clark | 32 | 1991-1995 | |
| 67 | Brett Cooksey | 32 | 1973-1975 | |
| 67 | Wayne Jenkins | 32 | 2015-2019 | |
| 67 | Daniel Martínez | 32 | 2003-2006 | |
| 67 | Santiago Martínez | 32 | 1978-1981 | |
| 67 | Artie Nava | 32 | 1992-1997 | |
| 67 | Tom Wheeler | 32 | 1970-1976 | |
| 76 | Gary Bowman | 31 | 1992-1996 | |
| 76 | Stanford Bryan | 31 | 1981-1985 | |
| 76 | Lloyd Cain | 31 | 1978-1984 | |
| 76 | Domingo Cruz | 31 | 1997-2003 | |
| 76 | Caden Edwards | 31 | 1972-1976 | |
| 76 | Carlos García | 31 | 2000-2001 | |
| 76 | Mark Griffin | 31 | 1996-2001 | |
| 76 | Joe Guelker | 31 | 1980-1986 | |
| 76 | Erwin Hagin | 31 | 1971-1976 | |
| 76 | Russ Hardy | 31 | 1994-1998 | |
| 76 | Ray Hartman | 31 | 1979-1985 | |
| 76 | Terence Henry | 31 | 1982-1986 | |
| 76 | Bailey Jackson | 31 | 1984-1991 | |
| 76 | Carlos Marín | 31 | 2001-2004 | |
| 76 | Alfonso Márquez | 31 | 1988-1989 | |
| 76 | Donovan Osborne | 31 | 2010-2015 | |
| 76 | Errol Powell | 31 | 1970-1976 | |
| 76 | Paul Sackett | 31 | 1984-1986 | |
| 76 | Donald Schmitt | 31 | 2016-2019 | |
| 76 | Beyene Thabiti | 31 | 1984-1987 | |
| 76 | Leonard Thompson | 31 | 1970-1974 | |
| 76 | António Tobías | 31 | 1984-1989 | |
| 76 | William Ware | 31 | 2001-2006 | |
| 99 | Hal Cross | 30 | 1974-1978 | |
| 99 | Alfredo Galindo | 30 | 1982-1986 |
