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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Archie Esparza# | .783 | 2025-2031 | |
| 2 | Joe Sparks | .730 | 2007-2019 | |
| 3 | Ian Richardson | .717 | 2009-2019 | |
| 4 | Kevin Schaefer | .698 | 2012-2023 | |
| 5 | Lee Myers# | .694 | 2019-2031 | |
| 6 | Jesús Bravo# | .687 | 2026-2031 | |
| 7 | Bob Jenkins* | .686 | 2008-2023 | |
| 8 | MacKenzie Gore# | .684 | 2026-2031 | |
| 9 | Joba Chamberlain | .682 | 2012-2027 | |
| 10 | Chad Billingsley | .677 | 2008-2024 | |
| 11 | José Torres# | .671 | 2026-2031 | |
| 11 | Zack Greinke* | .671 | 2005-2020 | |
| 13 | George Connolly# | .667 | 2018-2031 | |
| 14 | Noah Lowry | .663 | 2004-2015 | |
| 15 | Roger Clemens* | .655 | 1984-2006 | |
| 15 | Eddie Morgan* | .655 | 2005-2019 | |
| 17 | Keith McCoy# | .652 | 2020-2031 | |
| 18 | Nolan Arnold | .651 | 2011-2022 | |
| 19 | Anthony Hunt | .650 | 2016-2028 | |
| 20 | Jorge Flores# | .647 | 2025-2031 | |
| 21 | Juan Velázquez# | .644 | 2025-2031 | |
| 22 | Carlos Zambrano | .637 | 2001-2019 | |
| 23 | Júlio Pérez | .635 | 2007-2021 | |
| 23 | Madison Bumgarner | .635 | 2014-2031 | |
| 25 | Stan Combs# | .633 | 2023-2031 | |
| 25 | Garth Vaughn | .633 | 2008-2020 | |
| 27 | Justin Thompson | .632 | 2016-2026 | |
| 28 | Luis Anguiana# | .631 | 2026-2031 | |
| 28 | Heath Bell | .631 | 2004-2021 | |
| 30 | John Lambert# | .630 | 2022-2031 | |
| 31 | Dan Wilkerson# | .628 | 2023-2031 | |
| 32 | Ameirin Pavlenov | .627 | 2013-2021 | |
| 33 | Brandon Webb* | .626 | 2004-2024 | |
| 34 | Major Pixel | .624 | 2007-2021 | |
| 35 | Shelby Miller | .623 | 2016-2027 | |
| 36 | Tim Lincecum | .622 | 2009-2025 | |
| 37 | Felix Hernandez | .621 | 2009-2020 | |
| 37 | Jeff Shoemaker# | .621 | 2025-2031 | |
| 37 | Gregory Burke | .621 | 2002-2013 | |
| 40 | Rick Snow# | .620 | 2026-2031 | |
| 41 | Chip Blake# | .618 | 2022-2030 | |
| 42 | Andrew Bailey | .615 | 2010-2021 | |
| 42 | Brian Dalton | .615 | 2009-2018 | |
| 44 | Eddy Griffin# | .613 | 2020-2028 | |
| 44 | Toki Nagai | .613 | 2004-2015 | |
| 46 | CC Sabathia* | .608 | 2001-2019 | |
| 47 | Rick Ankiel | .607 | 1999-2015 | |
| 47 | Gilberto Martínez# | .607 | 2025-2031 | |
| 49 | Evan Coppinger# | .606 | 2020-2030 | |
| 50 | Chris Carpenter | .605 | 1997-2009 | |
| 51 | Allen Bailey | .604 | 2011-2023 | |
| 51 | Josh Johnson | .604 | 2010-2018 | |
| 53 | Micah Olson# | .603 | 2016-2031 | |
| 54 | Andy Ashby | .602 | 1991-2002 | |
| 54 | Paul Phelps | .602 | 2014-2026 | |
| 54 | Scott Kazmir | .602 | 2004-2019 | |
| 57 | Tim Pulliam# | .600 | 2026-2031 | |
| 58 | Jorge Enríquez# | .598 | 2020-2031 | |
| 59 | William Pierce# | .596 | 2025-2031 | |
| 60 | Cole Hamels* | .595 | 2007-2023 | |
| 60 | Dave Dowden | .595 | 2017-2027 | |
| 62 | Tommy Austin | .591 | 2014-2023 | |
| 62 | Kevin Pryor | .591 | 2012-2023 | |
| 64 | Jack Flaherty# | .588 | 2025-2031 | |
| 64 | Aaron Sele* | .588 | 1993-2006 | |
| 64 | António Ortíz | .588 | 2002-2011 | |
| 67 | Juan Guzman* | .587 | 1991-2005 | |
| 67 | Ryan Arnold | .587 | 2012-2021 | |
| 69 | Dylan Scott | .586 | 2007-2019 | |
| 69 | Dave Pownall | .586 | 2014-2027 | |
| 71 | Mark Prior* | .585 | 2002-2016 | |
| 71 | Bill Gill# | .585 | 2023-2031 | |
| 73 | Roy Ward | .584 | 2014-2026 | |
| 73 | Héctor Bernal# | .584 | 2024-2031 | |
| 75 | Randy D Johnson | .583 | 1988-2003 | |
| 76 | Ramon J Martinez | .582 | 1988-2002 | |
| 77 | Gary Lefebvre | .581 | 2002-2016 | |
| 77 | Pedro J Martinez | .581 | 1992-2007 | |
| 79 | Simon Duncombe | .579 | 2002-2017 | |
| 79 | Nathan Whalebelly | .579 | 2015-2029 | |
| 81 | Eduardo Prado# | .578 | 2020-2031 | |
| 82 | Ronald Moyer# | .577 | 2023-2031 | |
| 83 | Rodney Sánchez# | .576 | 2022-2031 | |
| 83 | Gerrit Cole# | .576 | 2022-2031 | |
| 85 | Angel Miranda | .574 | 1993-2006 | |
| 85 | Scott Randall | .574 | 2003-2020 | |
| 87 | Austin Willis | .573 | 2018-2027 | |
| 87 | Dwight Tucker | .573 | 2011-2027 | |
| 89 | Jake Peavy | .572 | 2002-2017 | |
| 90 | Fred Hawkins | .571 | 2019-2028 | |
| 90 | Ian Kennedy | .571 | 2010-2019 | |
| 90 | Roy Halladay* | .571 | 1998-2014 | |
| 90 | Pancho Ramírez# | .571 | 2025-2031 | |
| 90 | Sam Wilson | .571 | 2015-2024 | |
| 95 | Pedro Figueroa | .570 | 2012-2025 | |
| 96 | Mike Harkey | .569 | 1988-2004 | |
| 96 | Javier Vazquez* | .569 | 1998-2013 | |
| 96 | Richard Verhoeve# | .569 | 2026-2031 | |
| 96 | Steve Woodard | .569 | 1997-2014 | |
| 96 | Stephen Strasburg | .569 | 2011-2027 |
