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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | José Encarnación | 64 | 1984-1991 | |
| 2 | Carlos Cervantes | 49 | 1977-1982 | |
| 3 | Leo Chambers | 47 | 1997-2002 | |
| 4 | Tristan Lang | 45 | 1977-1981 | |
| 4 | Mike Smith | 45 | 2010-2015 | |
| 6 | Andre Frye | 43 | 1982-1987 | |
| 6 | Ken May | 43 | 1983-1988 | |
| 8 | Danny Copeland | 42 | 1970-1973 | |
| 9 | Bill Hall | 41 | 1978-1984 | |
| 9 | Daniel Jefferson | 41 | 1977-1983 | |
| 11 | William Bertrand | 40 | 1980-1983 | |
| 11 | Lyndon Breary | 40 | 1974-1979 | |
| 11 | Armando Gutiérrez | 40 | 1970-1976 | |
| 14 | John Allen | 39 | 1980-1985 | |
| 14 | Jon Brown | 39 | 1976-1980 | |
| 14 | Floyd Cash | 39 | 1980-1986 | |
| 14 | Mario Jaramillo | 39 | 1970-1976 | |
| 14 | Eugene Jenkins | 39 | 2004-2009 | |
| 14 | Luis Ortíz | 39 | 1970-1976 | |
| 14 | Rubén Rodríguez | 39 | 1990-1994 | |
| 21 | Jesse Bennett | 38 | 1979-1984 | |
| 21 | Jack Carver | 38 | 2002-2007 | |
| 23 | Eddie Acosta | 36 | 1995-2001 | |
| 23 | Bob Ladd | 36 | 1994-2000 | |
| 23 | Randolph Parker | 36 | 1980-1983 | |
| 26 | Jimmy Carr | 35 | 1988-1994 | |
| 26 | Alfonso De Jesús | 35 | 1990-1995 | |
| 26 | Luis Galloca | 35 | 2011-2018 | |
| 26 | Francisco González | 35 | 1981-1986 | |
| 26 | Gunnar McFalls | 35 | 2006-2012 | |
| 26 | José Romano | 35 | 1970-1973 | |
| 26 | Adam Sherman | 35 | 1974-1976 | |
| 26 | Rick Thompson | 35 | 2009-2016 | |
| 34 | Curt Allen | 34 | 1988-1994 | |
| 34 | Al Cahill | 34 | 2007-2013 | |
| 34 | Pedro Cortéz | 34 | 1974-1976 | |
| 34 | Frank Miller | 34 | 2001-2007 | |
| 34 | William Shaw | 34 | 1992-1996 | |
| 39 | Oscar Hendricks | 33 | 2002-2005 | |
| 39 | Luis Manuel López | 33 | 1987-1988 | |
| 39 | Colin Moore | 33 | 1986-1991 | |
| 39 | Manuel Pérez | 33 | 1978-1981 | |
| 39 | Deron Rush | 33 | 1980-1982 | |
| 44 | Colton Brown | 32 | 1989-1991 | |
| 44 | Will Byrd | 32 | 1970-1973 | |
| 44 | Peter Clarke | 32 | 1978-1982 | |
| 44 | Terence Henry | 32 | 1980-1982 | |
| 44 | Evan Jones | 32 | 1987-1993 | |
| 44 | Kenneth Williams | 32 | 1977-1979 | |
| 50 | Jeff Farris | 31 | 1993-1999 | |
| 50 | Fernando González | 31 | 1991-1995 | |
| 50 | Jesús González | 31 | 1996-2001 | |
| 50 | Ken Hughes | 31 | 2011-2018 | |
| 50 | Alfonso Márquez | 31 | 1986-1991 | |
| 50 | Walter Mason | 31 | 1990-1992 | |
| 50 | Jeffrey McKenzie | 31 | 1993-1995 | |
| 50 | Ánibal Méndez | 31 | 1988-1992 | |
| 50 | Freddie Wagner | 31 | 1976-1979 | |
| 59 | Oscar Benson | 30 | 1991-1994 | |
| 59 | Lúcio Dávila | 30 | 1983-1985 | |
| 59 | Derek Dougherty | 30 | 1980-1985 | |
| 59 | John Graves | 30 | 1985-1990 | |
| 59 | Brian Kline | 30 | 1979-1981 | |
| 59 | Alonso Ordóńez | 30 | 1976-1979 | |
| 59 | Felipe Pineda | 30 | 1977-1982 | |
| 59 | Clement Stevens | 30 | 1987-1991 | |
| 59 | Jonathan Thomas | 30 | 1995-1998 | |
| 59 | Joe Wells | 30 | 1999-2003 | |
| 59 | Geoff Williams | 30 | 1976-1978 | |
| 70 | Felipe Álvarez | 29 | 1980-1982 | |
| 70 | Julius Anderson | 29 | 1994-1999 | |
| 70 | Mike Blake | 29 | 1978-1984 | |
| 70 | Kurt Bullard | 29 | 1992-1996 | |
| 70 | Tony Callahan | 29 | 2007-2012 | |
| 70 | Duane Herring | 29 | 1988-1994 | |
| 70 | Peter Hubbard | 29 | 2009-2013 | |
| 70 | Kevin McDonald | 29 | 1988-1991 | |
| 70 | Joe McDowell | 29 | 1994-2000 | |
| 70 | Erik Porter | 29 | 1973-1975 | |
| 70 | Roy Ray# | 29 | 2013-2015 | |
| 70 | Tim Roney | 29 | 1982-1988 | |
| 70 | Kent Shaffer | 29 | 1984-1991 | |
| 70 | Jason Stanley | 29 | 2001-2007 | |
| 70 | Jamal Walker | 29 | 2001-2007 | |
| 70 | Bill Wellings | 29 | 1996-1999 | |
| 70 | Will Williamson | 29 | 2003-2006 | |
| 87 | Kent Beddall | 28 | 1978-1981 | |
| 87 | Plinio Blanco | 28 | 1997-2001 | |
| 87 | Ray Brown | 28 | 1986-1988 | |
| 87 | Chung Chia | 28 | 1982-1987 | |
| 87 | Collin Clark | 28 | 2000-2002 | |
| 87 | Matt Crouch | 28 | 1973-1976 | |
| 87 | Luis Guerrero | 28 | 1996-1997 | |
| 87 | Michael Hill | 28 | 1970-1972 | |
| 87 | Joey Hoover | 28 | 1983-1988 | |
| 87 | Patrick Kidd | 28 | 1982-1985 | |
| 87 | Manuel Morales | 28 | 1994-1998 | |
| 87 | Luis Nevárez | 28 | 1987-1989 | |
| 87 | Gerald Sanford# | 28 | 2018-2023 | |
| 87 | Jim Steele | 28 | 1982-1984 |
