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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | John Wood# | .2232 | 2029-2031 | |
| 2 | Matt J Miller | .2376 | 2003-2016 | |
| 3 | Dan Woods# | .2443 | 2023-2031 | |
| 4 | Alfredo Gómez# | .2621 | 2028-2031 | |
| 5 | Luis Anguiana# | .2703 | 2026-2031 | |
| 6 | Heath Bell | .2705 | 2004-2021 | |
| 7 | Paul Hale# | .2735 | 2020-2031 | |
| 8 | John Christensen | .2774 | 2015-2024 | |
| 9 | Ignacio Reyes# | .2806 | 2028-2031 | |
| 10 | Roger Bailey | .2814 | 2003-2014 | |
| 11 | Mark Prior* | .2889 | 2002-2016 | |
| 12 | Francisco Ramírez# | .2911 | 2017-2030 | |
| 13 | Brad Cochran | .2917 | 2019-2027 | |
| 14 | Joel Zumaya | .2951 | 2011-2023 | |
| 15 | Jason Dickson | .2975 | 1997-2006 | |
| 16 | Roger Clemens* | .2999 | 1984-2006 | |
| 17 | Randy D Johnson | .3003 | 1988-2003 | |
| 18 | Jason Ellis | .3039 | 2013-2027 | |
| 19 | Dan White | .3050 | 2012-2021 | |
| 19 | Thomas Rice# | .3050 | 2017-2031 | |
| 21 | António Ortíz | .3089 | 2002-2011 | |
| 22 | Ryan Arnold | .3103 | 2012-2021 | |
| 23 | Bryan Kent# | .3155 | 2025-2031 | |
| 24 | Erik Bedard | .3184 | 2004-2013 | |
| 25 | Gilberto Martínez# | .3194 | 2025-2031 | |
| 26 | Clifton Jackson# | .3204 | 2024-2029 | |
| 27 | Ian Kennedy | .3214 | 2010-2019 | |
| 28 | Héctor Bernal# | .3231 | 2024-2031 | |
| 29 | Charlie Frohwirth | .3270 | 2012-2024 | |
| 30 | Justin Thompson | .3281 | 2016-2026 | |
| 31 | A J Burnett | .3284 | 1999-2010 | |
| 32 | Bob Schultz | .3304 | 2013-2022 | |
| 33 | Joakim Soria | .3307 | 2012-2022 | |
| 34 | Jose A Nunez | .3308 | 2001-2012 | |
| 35 | Scott Sanders | .3320 | 1993-2007 | |
| 36 | Dennis Redden# | .3346 | 2029-2031 | |
| 37 | Adrian Ackermann | .3359 | 2014-2022 | |
| 37 | Jonathan Papelbon | .3359 | 2008-2021 | |
| 39 | Carlos Jiménez# | .3361 | 2021-2031 | |
| 40 | Raúl López | .3389 | 2000-2016 | |
| 41 | Dusty Massey# | .3404 | 2019-2025 | |
| 41 | Kevin Walters | .3404 | 2003-2015 | |
| 43 | Jon Lester | .3419 | 2008-2021 | |
| 44 | Daniel Patterson | .3428 | 2017-2029 | |
| 45 | Henry Moss# | .3444 | 2019-2029 | |
| 46 | Ronald Moyer# | .3445 | 2023-2031 | |
| 47 | Santiago Herrera | .3450 | 2000-2018 | |
| 48 | Roy Halladay* | .3457 | 1998-2014 | |
| 49 | Amdre Nova# | .3468 | 2030-2031 | |
| 50 | Jeff Samardzija | .3477 | 2009-2021 | |
| 51 | Stan Combs# | .3491 | 2023-2031 | |
| 52 | Cisco Castellanos# | .3493 | 2025-2031 | |
| 53 | Duane Wilson | .3517 | 2008-2020 | |
| 54 | Barry Zito | .3525 | 2000-2014 | |
| 55 | Jerry Patterson | .3526 | 2002-2015 | |
| 56 | Chad Billingsley | .3534 | 2008-2024 | |
| 57 | Ken Brandon | .3574 | 2019-2029 | |
| 58 | Brandon Webb* | .3579 | 2004-2024 | |
| 59 | Chad Qualls | .3590 | 2006-2020 | |
| 60 | Jake Peavy | .3594 | 2002-2017 | |
| 61 | Allen Bailey | .3597 | 2011-2023 | |
| 62 | Eduardo Vázquez# | .3600 | 2023-2030 | |
| 63 | Brett Tomko | .3603 | 1997-2004 | |
| 64 | Máximo Sánchez | .3608 | 2015-2025 | |
| 65 | Zack Greinke* | .3613 | 2005-2020 | |
| 66 | Eric Hurley | .3619 | 2007-2020 | |
| 67 | Tim Pulliam# | .3622 | 2026-2031 | |
| 68 | Rick Cederberg# | .3630 | 2025-2031 | |
| 69 | Leo Erickson# | .3636 | 2022-2029 | |
| 70 | Daron Maddox | .3639 | 2015-2027 | |
| 70 | Jeff Shoemaker# | .3639 | 2025-2031 | |
| 72 | Adelphos Papademetriou | .3642 | 2002-2011 | |
| 72 | Matt Morris | .3642 | 1997-2005 | |
| 72 | David Price | .3642 | 2011-2019 | |
| 75 | Anderson Fergerson | .3647 | 2014-2028 | |
| 76 | Shelby Miller | .3652 | 2016-2027 | |
| 77 | Bob Jenkins* | .3658 | 2008-2023 | |
| 78 | Raúl Mateo# | .3660 | 2026-2031 | |
| 78 | Felix Hernandez | .3660 | 2009-2020 | |
| 80 | Jorge Flores# | .3665 | 2025-2031 | |
| 81 | Jimmy Anderson | .3668 | 1999-2011 | |
| 82 | Dave Pownall | .3676 | 2014-2027 | |
| 83 | Eldon Hernández | .3684 | 2018-2026 | |
| 84 | Micah Olson# | .3690 | 2016-2031 | |
| 85 | David Nied* | .3694 | 1992-2009 | |
| 86 | Carlos Durán# | .3696 | 2028-2031 | |
| 87 | José Torres# | .3734 | 2026-2031 | |
| 88 | Joba Chamberlain | .3743 | 2012-2027 | |
| 89 | Wilford Chambers* | .3745 | 2006-2025 | |
| 89 | Dan Wilkerson# | .3745 | 2023-2031 | |
| 89 | Ismael Valdez* | .3745 | 1994-2010 | |
| 92 | Jack Flaherty# | .3750 | 2025-2031 | |
| 92 | Aaron Sele* | .3750 | 1993-2006 | |
| 94 | Raimondo Amberezzio# | .3756 | 2026-2031 | |
| 95 | Major Pixel | .3770 | 2007-2021 | |
| 96 | CC Sabathia* | .3777 | 2001-2019 | |
| 96 | Kevin Schaefer | .3777 | 2012-2023 | |
| 98 | Steve Nebraska | .3782 | 2005-2018 | |
| 99 | Eddie Morgan* | .3785 | 2005-2019 | |
| 100 | Tommy Austin | .3788 | 2014-2023 |
