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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Jared Small | .741 | 2040-2050 | |
| 2 | Jared Kozlowski | .737 | 2055-2068 | |
| 3 | Alberto García | .710 | 2034-2048 | |
| 4 | Roberto Martinez | .708 | 2067-2075 | |
| 5 | Larry Daig# | .707 | 2065-2075 | |
| 6 | Luis Delgado | .701 | 2020-2034 | |
| 7 | Danny Ottamendi | .695 | 2053-2061 | |
| 8 | Dan Winston | .693 | 2013-2026 | |
| 9 | Robert Dorsey | .691 | 2012-2019 | |
| 10 | Jorge Blanco | .674 | 2032-2045 | |
| 10 | Brian Jackson | .674 | 2058-2067 | |
| 12 | Mitsuhiro Nishimura | .673 | 2059-2068 | |
| 13 | Seth Slade | .671 | 2029-2044 | |
| 14 | Naruhiko Abe | .670 | 2028-2039 | |
| 15 | Joe Larson | .667 | 2039-2051 | |
| 16 | Franky Santegoeds | .662 | 2053-2065 | |
| 17 | Boyd Burnett | .660 | 1997-2001 | |
| 17 | David Ford | .660 | 2011-2016 | |
| 19 | Joe Coffman | .657 | 2000-2017 | |
| 20 | Marcos Rodríguez | .656 | 2015-2024 | |
| 21 | Tom Moore | .652 | 2035-2047 | |
| 22 | Francisco Marés | .651 | 1994-2004 | |
| 23 | Ernie Christian | .650 | 1990-2004 | |
| 24 | Gerald Sullivan | .646 | 2024-2033 | |
| 25 | Neville Roosemont | .645 | 2053-2067 | |
| 26 | Enrique Colón | .644 | 2028-2035 | |
| 27 | Folkert Scherpenisse | .642 | 2061-2070 | |
| 28 | Vern Garbie# | .639 | 2061-2075 | |
| 28 | Josh Gesler | .639 | 2044-2057 | |
| 30 | Ricardo Díaz | .637 | 2000-2010 | |
| 31 | Henry Bader | .636 | 1999-2012 | |
| 31 | Victor Pire | .636 | 2059-2072 | |
| 33 | Craig Walker | .634 | 1991-1999 | |
| 34 | Bryan Banks | .633 | 1998-2002 | |
| 35 | Tony Webber | .631 | 2061-2071 | |
| 36 | Matt Roberts | .628 | 2004-2016 | |
| 37 | Brian Renton | .620 | 2037-2047 | |
| 38 | Aaron Carter | .619 | 2011-2021 | |
| 38 | Juan Cardenas | .619 | 2000-2010 | |
| 40 | Dan Burford | .615 | 2030-2037 | |
| 41 | Andrew Cramer | .613 | 2033-2040 | |
| 42 | Mike Freeman | .609 | 2056-2071 | |
| 43 | Elwood Bruce# | .604 | 2062-2075 | |
| 43 | Claudio Mesa | .604 | 2041-2049 | |
| 43 | Henry Williams | .604 | 2036-2042 | |
| 46 | David Picot | .602 | 1996-2002 | |
| 47 | Jorge Ochoa | .600 | 2017-2023 | |
| 47 | Juan Valdéz | .600 | 1996-2003 | |
| 49 | Brandon Benoit | .599 | 2035-2051 | |
| 50 | Ken Pilgrim | .598 | 2018-2025 | |
| 50 | Dennis Hartman | .598 | 2050-2064 | |
| 52 | Mike Parsons | .597 | 2031-2038 | |
| 53 | Dino Talenti | .596 | 2039-2052 | |
| 54 | Bill Carr | .595 | 2037-2047 | |
| 54 | José Chávez | .595 | 1994-2001 | |
| 56 | Julian Braber | .594 | 2034-2050 | |
| 57 | Teodor Reyes | .593 | 1999-2008 | |
| 57 | Ramón Ramírez | .593 | 1995-2007 | |
| 59 | Fred Lee | .592 | 1998-2002 | |
| 60 | Vincente González | .591 | 2024-2035 | |
| 61 | Gabriel González | .590 | 2007-2018 | |
| 61 | Cruz Varela | .590 | 2058-2067 | |
| 61 | Vaughn Gibson | .590 | 1997-2007 | |
| 64 | António Alvarado | .589 | 1990-1996 | |
| 65 | Jason Rogers | .588 | 2038-2047 | |
| 66 | Roland Ellenberger | .585 | 2060-2074 | |
| 67 | Thomas Barrett | .583 | 2009-2018 | |
| 67 | Brendon Terry | .583 | 2010-2017 | |
| 69 | Marco Orosco | .582 | 2063-2072 | |
| 69 | Ed Rawls | .582 | 2036-2050 | |
| 71 | Stu Winkle | .581 | 2031-2047 | |
| 71 | Zach Brocklebank | .581 | 2051-2059 | |
| 71 | Ramon Gonzalez | .581 | 2061-2071 | |
| 71 | Hiroshige Uchida | .581 | 2000-2018 | |
| 75 | António Florita | .580 | 2052-2064 | |
| 75 | Norbert Kooiman | .580 | 2024-2036 | |
| 75 | George Lloyd | .580 | 2032-2047 | |
| 78 | Hwui-ning Ling | .579 | 2001-2014 | |
| 79 | Warner Cavanagh | .578 | 2044-2062 | |
| 80 | Scott Hall | .577 | 2033-2039 | |
| 80 | Júlio Pérez | .577 | 2005-2013 | |
| 82 | Ryan Moore | .576 | 2024-2036 | |
| 82 | Gjelt van den Bovenkamp | .576 | 2061-2069 | |
| 84 | Sterling Lee | .574 | 2003-2011 | |
| 85 | Vic Valenzuela | .573 | 2052-2066 | |
| 85 | Raynard Keller | .573 | 2057-2068 | |
| 87 | Christopher Wicks | .572 | 1997-2007 | |
| 88 | Masaaki Araki | .571 | 2058-2068 | |
| 88 | Dave Callahan | .571 | 2039-2050 | |
| 90 | Julian Phillips | .569 | 2004-2014 | |
| 91 | Les Saunders | .568 | 1990-1998 | |
| 91 | Yuniesky Fritze | .568 | 2061-2073 | |
| 91 | Gerardo Caraballo | .568 | 2035-2051 | |
| 91 | Fedele Runggaldier | .568 | 2063-2072 | |
| 95 | Miguel Hurtado | .567 | 2056-2073 | |
| 96 | Jose Miranda | .566 | 2058-2067 | |
| 96 | Kenny Bradley | .566 | 1998-2011 | |
| 98 | Nolan Park | .564 | 2029-2038 | |
| 98 | Pedro Salazar | .564 | 2030-2039 | |
| 100 | Félix Rodríguez | .562 | 1992-2008 |
