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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Adrian Ackermann | 1.000 | 2014-2022 | |
| 1 | Raúl Aguilar# | 1.000 | 2020-2031 | |
| 1 | Jason Dickson | 1.000 | 1997-2006 | |
| 1 | Eldon Hernández | 1.000 | 2018-2026 | |
| 1 | Mark McDonald | 1.000 | 2014-2025 | |
| 1 | António Ortíz | 1.000 | 2002-2011 | |
| 1 | Chad Qualls | 1.000 | 2006-2020 | |
| 1 | Brett Tomko | 1.000 | 1997-2004 | |
| 1 | John Wood# | 1.000 | 2029-2031 | |
| 1 | Malcolm Zegwaard | 1.000 | 2013-2020 | |
| 11 | Wade Miller | .857 | 1999-2012 | |
| 12 | Charlie Frohwirth | .833 | 2012-2024 | |
| 12 | Santiago Herrera | .833 | 2000-2018 | |
| 12 | Matt J Miller | .833 | 2003-2016 | |
| 15 | Jeff Shoemaker# | .818 | 2025-2031 | |
| 16 | Randy D Johnson | .800 | 1988-2003 | |
| 16 | Byung-Hyun Kim | .800 | 1999-2014 | |
| 16 | Dave Márquez | .800 | 2017-2029 | |
| 16 | Nathan Whalebelly | .800 | 2015-2029 | |
| 20 | Kevin Walters | .786 | 2003-2015 | |
| 21 | Kevin Gregg | .778 | 2004-2017 | |
| 22 | Jim Anderson# | .750 | 2019-2025 | |
| 22 | Ryan Arnold | .750 | 2012-2021 | |
| 22 | Heath Bell | .750 | 2004-2021 | |
| 22 | A J Burnett | .750 | 1999-2010 | |
| 22 | Roger Clemens* | .750 | 1984-2006 | |
| 22 | Jack Flaherty# | .750 | 2025-2031 | |
| 22 | Roy Halladay* | .750 | 1998-2014 | |
| 22 | Ramon J Martinez | .750 | 1988-2002 | |
| 22 | Guillermo Mota | .750 | 1999-2010 | |
| 22 | Amdre Nova# | .750 | 2030-2031 | |
| 22 | David Price | .750 | 2011-2019 | |
| 22 | Kumar Rocker# | .750 | 2020-2026 | |
| 22 | Patrick Thompson | .750 | 2013-2023 | |
| 22 | Irving Townsend# | .750 | 2026-2031 | |
| 36 | George Connolly# | .742 | 2018-2031 | |
| 37 | R A Dickey | .727 | 2002-2018 | |
| 37 | Jerry Patterson | .727 | 2002-2015 | |
| 37 | Tim Pulliam# | .727 | 2026-2031 | |
| 40 | Raúl Mateo# | .714 | 2026-2031 | |
| 40 | Kevin Schaefer | .714 | 2012-2023 | |
| 40 | Brandon Webb* | .714 | 2004-2024 | |
| 43 | Allen Bailey | .706 | 2011-2023 | |
| 43 | Roy Oswalt* | .706 | 2001-2016 | |
| 45 | Raimondo Amberezzio# | .700 | 2026-2031 | |
| 45 | Steve Karsay | .700 | 1993-2007 | |
| 47 | Chad Billingsley | .684 | 2008-2024 | |
| 48 | Roger Bailey | .667 | 2003-2014 | |
| 48 | Wilford Chambers* | .667 | 2006-2025 | |
| 48 | Robert Dixon# | .667 | 2019-2031 | |
| 48 | Andre Ford | .667 | 2018-2023 | |
| 48 | Eddy Griffin# | .667 | 2020-2028 | |
| 48 | John Halama | .667 | 1998-2008 | |
| 48 | Cole Hamels* | .667 | 2007-2023 | |
| 48 | Alfredo Huerta# | .667 | 2022-2030 | |
| 48 | Carlos Jiménez# | .667 | 2021-2031 | |
| 48 | Gabe Johnson | .667 | 2019-2028 | |
| 48 | John Lambert# | .667 | 2022-2031 | |
| 48 | Raúl López | .667 | 2000-2016 | |
| 48 | Javier Martínez# | .667 | 2021-2026 | |
| 48 | Ronald Moyer# | .667 | 2023-2031 | |
| 48 | Brad Radke | .667 | 1995-2007 | |
| 48 | Francisco Ramírez# | .667 | 2017-2030 | |
| 48 | Jeff Samardzija | .667 | 2009-2021 | |
| 48 | Chris Sharp# | .667 | 2021-2031 | |
| 48 | John Smoltz | .667 | 1988-2003 | |
| 48 | Al Taylor | .667 | 2019-2026 | |
| 48 | Javier Vazquez* | .667 | 1998-2013 | |
| 48 | Joel Zumaya | .667 | 2011-2023 | |
| 70 | Madison Bumgarner | .654 | 2014-2031 | |
| 70 | Zack Greinke* | .654 | 2005-2020 | |
| 72 | Jose Acevedo | .643 | 2002-2013 | |
| 73 | Daron Maddox | .636 | 2015-2027 | |
| 74 | Ken Brandon | .625 | 2019-2029 | |
| 74 | Frank Larkin | .625 | 2000-2011 | |
| 74 | Gary Lefebvre | .625 | 2002-2016 | |
| 74 | Roger Powell | .625 | 2020-2028 | |
| 78 | Andy Ashby | .615 | 1991-2002 | |
| 78 | Daniel Patterson | .615 | 2017-2029 | |
| 80 | George Burke# | .600 | 2019-2029 | |
| 80 | Rick Cederberg# | .600 | 2025-2031 | |
| 80 | Xavier Ford# | .600 | 2023-2031 | |
| 80 | Alfredo Gómez# | .600 | 2028-2031 | |
| 80 | Bob Jenkins* | .600 | 2008-2023 | |
| 80 | Gilberto Martínez# | .600 | 2025-2031 | |
| 80 | Eddie Morgan* | .600 | 2005-2019 | |
| 80 | Jose A Nunez | .600 | 2001-2012 | |
| 80 | Joe Powell | .600 | 2002-2016 | |
| 80 | Kyle Sackett | .600 | 2000-2015 | |
| 80 | Tito Smith# | .600 | 2020-2031 | |
| 80 | José Torres# | .600 | 2026-2031 | |
| 80 | Eduardo Vázquez# | .600 | 2023-2030 | |
| 80 | Dan White | .600 | 2012-2021 | |
| 80 | Randy Wolf | .600 | 1999-2013 | |
| 95 | Joba Chamberlain | .586 | 2012-2027 | |
| 96 | Reece MacKinley | .583 | 2007-2024 | |
| 97 | Chip Blake# | .571 | 2022-2030 | |
| 97 | Simon Duncombe | .571 | 2002-2017 | |
| 97 | Carlos Durán# | .571 | 2028-2031 | |
| 97 | Tim Hudson | .571 | 1999-2011 |
