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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Scott Schowalter | .2222 | 2012-2021 | |
| 2 | Chris Mattison | .2381 | 2012-2019 | |
| 3 | Rich Forbes# | .2654 | 2013-2025 | |
| 4 | Corey Johnson | .2659 | 2010-2020 | |
| 5 | Sergio Martinez | .2684 | 2005-2017 | |
| 6 | Carlos Pardo | .2696 | 2012-2021 | |
| 7 | Hector Moralez | .2764 | 2011-2019 | |
| 8 | Chris Johnson | .2867 | 2007-2018 | |
| 9 | Andy Dooley# | .2886 | 2014-2025 | |
| 10 | William Deel# | .2903 | 2022-2025 | |
| 11 | Corbett Wright | .2935 | 2010-2024 | |
| 12 | Santos Martinez | .2986 | 2000-2012 | |
| 13 | Chris Jacoby# | .2993 | 2015-2025 | |
| 13 | Todd Thompson# | .2993 | 2015-2025 | |
| 15 | Oscar Martinez | .3006 | 2000-2010 | |
| 16 | Nelson Cirilo | .3043 | 2007-2014 | |
| 17 | Stephen Stride | .3046 | 2011-2022 | |
| 18 | Nick Slover# | .3119 | 2022-2025 | |
| 19 | Jose Rodriguez* | .3123 | 2000-2016 | |
| 20 | Aaron Sutton | .3131 | 2009-2021 | |
| 21 | Chris Booth# | .3194 | 2019-2025 | |
| 22 | Gordie Clifford# | .3271 | 2013-2024 | |
| 23 | Cameron Hutchinson# | .3273 | 2015-2025 | |
| 24 | Tom Kitko | .3309 | 2012-2023 | |
| 25 | Alejandro Marquina | .3333 | 2002-2016 | |
| 26 | Justin Turbeville | .3355 | 2008-2018 | |
| 27 | Brett Dorman | .3377 | 2005-2019 | |
| 28 | Brad Hower | .3391 | 2010-2024 | |
| 29 | Dave Harvey# | .3401 | 2020-2025 | |
| 30 | Brian Prince | .3403 | 2011-2024 | |
| 31 | Paul Ledford* | .3415 | 2000-2013 | |
| 32 | Dan Mills# | .3425 | 2014-2025 | |
| 33 | Jordan Clarke | .3426 | 2004-2023 | |
| 34 | Phil Gregoire# | .3434 | 2013-2025 | |
| 35 | Matt Graham# | .3436 | 2020-2025 | |
| 36 | Hiromi Fukuda | .3443 | 2006-2018 | |
| 37 | Dan Miller# | .3468 | 2018-2025 | |
| 37 | Takeji Takano# | .3468 | 2024-2025 | |
| 39 | Francisco Camacho | .3506 | 2000-2013 | |
| 40 | Chris Frost | .3543 | 2011-2022 | |
| 41 | Branden Covington# | .3563 | 2024-2025 | |
| 42 | Chris Harris | .3564 | 2007-2020 | |
| 43 | Hethum Manasarian | .3580 | 2001-2020 | |
| 44 | Barry McLamb# | .3582 | 2013-2023 | |
| 45 | Zachary Facundo | .3586 | 2000-2009 | |
| 46 | Jose Ojeda# | .3589 | 2020-2025 | |
| 47 | Josh Shute | .3592 | 2013-2018 | |
| 48 | Seth Dann | .3603 | 2002-2013 | |
| 49 | Xiang-ling Fei* | .3606 | 2000-2012 | |
| 50 | Heriberto Milan | .3622 | 2007-2022 | |
| 51 | Julian Bryant# | .3636 | 2020-2025 | |
| 52 | Adam Farmer | .3679 | 2000-2009 | |
| 53 | Josh Huggins# | .3681 | 2022-2025 | |
| 54 | Aubrey Morrison | .3684 | 2000-2011 | |
| 55 | Chris Bentley | .3691 | 2008-2020 | |
| 56 | Rodrigo Lemus# | .3710 | 2013-2025 | |
| 57 | Danny Offen# | .3715 | 2020-2025 | |
| 58 | Casey Abbott# | .3718 | 2009-2025 | |
| 59 | Johnny Keener# | .3726 | 2015-2025 | |
| 60 | Roberto Salazar# | .3739 | 2013-2025 | |
| 61 | Jeff Buck# | .3740 | 2015-2025 | |
| 62 | Daishin Uchida | .3750 | 2008-2016 | |
| 63 | Joe Hart# | .3756 | 2013-2025 | |
| 64 | Pat Payne | .3757 | 2009-2023 | |
| 65 | Luke Scrimger# | .3763 | 2019-2025 | |
| 66 | Pat Hovhannisian# | .3793 | 2014-2025 | |
| 67 | Jonathan Allen# | .3795 | 2016-2025 | |
| 68 | Kory Tourville | .3799 | 2014-2024 | |
| 69 | Oreste Comollo | .3840 | 2001-2014 | |
| 70 | Sean Stevens# | .3853 | 2023-2025 | |
| 71 | Adam D'Alberto# | .3860 | 2016-2025 | |
| 72 | Geremia Farinelli | .3866 | 2000-2014 | |
| 73 | Bill Vasquez | .3872 | 2000-2012 | |
| 74 | Justin Jemison# | .3897 | 2019-2025 | |
| 75 | Josh Flaten# | .3910 | 2015-2025 | |
| 76 | J.R. Mitchell# | .3921 | 2013-2025 | |
| 77 | Miguel Berrios# | .3927 | 2018-2025 | |
| 78 | Andy Weatherholt# | .3942 | 2021-2025 | |
| 79 | Adrian Radecki | .3949 | 2012-2019 | |
| 80 | Adam Ryan# | .3967 | 2017-2024 | |
| 81 | Iliana Preciado | .4000 | 2000-2009 | |
| 82 | Blake Barber | .4007 | 2000-2007 | |
| 83 | Bill Flowers# | .4012 | 2011-2025 | |
| 84 | Carlos Garcia | .4017 | 2000-2014 | |
| 85 | Albert Fabian# | .4019 | 2014-2025 | |
| 86 | Tyrone Hairston | .4022 | 2002-2013 | |
| 87 | Antonio Higuera# | .4043 | 2007-2025 | |
| 88 | Corey Gruver# | .4056 | 2006-2025 | |
| 89 | Jorge Lopez | .4060 | 2004-2013 | |
| 90 | Alfredo Tiscareno# | .4070 | 2010-2025 | |
| 91 | Cody Morosko | .4087 | 2000-2010 | |
| 92 | Sean Bartol | .4105 | 2000-2010 | |
| 93 | Andres Encarnacion | .4135 | 2000-2011 | |
| 94 | Matt Schmid# | .4147 | 2013-2023 | |
| 95 | Travis Thurber# | .4161 | 2005-2024 | |
| 96 | Seth Carey | .4171 | 2004-2016 | |
| 97 | Ryan Henry# | .4173 | 2022-2025 | |
| 98 | William Arredondo | .4174 | 2000-2012 | |
| 99 | Ron Baumgardner | .4182 | 2010-2019 | |
| 100 | Greg Sandlin | .4188 | 2009-2024 |
