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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Gabe Vincent | .3238 | 2012-2023 | |
| 2 | Cameron Outlaw# | .3313 | 2015-2025 | |
| 3 | Federico Gonzalez | .3329 | 2000-2009 | |
| 4 | Adam Arnett | .3378 | 2000-2009 | |
| 5 | Sean Cofield | .3386 | 2011-2021 | |
| 6 | Billy Merner# | .3401 | 2015-2025 | |
| 7 | Enrique Perez | .3416 | 2009-2017 | |
| 8 | Mike Felder | .3490 | 2004-2014 | |
| 9 | Tom Rise# | .3512 | 2015-2024 | |
| 10 | Tom Schauman | .3515 | 2003-2010 | |
| 11 | Terry Droubay# | .3530 | 2017-2025 | |
| 12 | Luis Alcoser | .3539 | 2005-2022 | |
| 13 | Mauricio Martinez | .3556 | 2015-2024 | |
| 14 | Brian Gann | .3558 | 2000-2013 | |
| 15 | C.J. Mejia | .3561 | 2011-2019 | |
| 16 | Rick Winkler# | .3579 | 2017-2024 | |
| 17 | Nick Kline | .3585 | 2007-2023 | |
| 17 | Josh Bass# | .3585 | 2014-2025 | |
| 19 | Justin Baker# | .3593 | 2015-2025 | |
| 20 | Nate Briceno# | .3595 | 2014-2025 | |
| 21 | Andy Jackson | .3639 | 2005-2013 | |
| 22 | Ryan Hester | .3649 | 2001-2011 | |
| 23 | Isaiah Robinson# | .3677 | 2018-2025 | |
| 24 | Jesus Quintero | .3681 | 2000-2009 | |
| 25 | Kyle Connell# | .3691 | 2015-2025 | |
| 26 | Justin Steach | .3708 | 2004-2014 | |
| 27 | Brad Goodman | .3730 | 2012-2021 | |
| 28 | Chris Pickens | .3734 | 2005-2013 | |
| 29 | Cameron Brown | .3750 | 2011-2018 | |
| 30 | Chris Marquis# | .3752 | 2018-2025 | |
| 31 | Don Sheffield | .3759 | 2000-2011 | |
| 32 | Jonathan Parker | .3762 | 2011-2022 | |
| 33 | Josh Adams | .3775 | 2000-2014 | |
| 34 | Ramon Sandoval | .3776 | 2000-2009 | |
| 35 | Nick Giese | .3797 | 2000-2009 | |
| 36 | Arturo Jimenez | .3812 | 2003-2013 | |
| 37 | Justin Messer | .3814 | 2000-2012 | |
| 38 | Aaron Harrison | .3819 | 2000-2010 | |
| 39 | Edgar Gonzalez | .3829 | 2000-2009 | |
| 40 | Tadanori Kawasaki | .3833 | 2005-2014 | |
| 41 | Brian Yates | .3871 | 2003-2012 | |
| 42 | Jeremy Excell | .3877 | 2000-2012 | |
| 43 | Santiago Rodas | .3886 | 2000-2010 | |
| 44 | Nelson Martinez# | .3894 | 2011-2023 | |
| 45 | Jose Estrada | .3900 | 2000-2010 | |
| 46 | Tyler Byrd | .3905 | 2000-2011 | |
| 47 | Jonathan McMahon | .3950 | 2001-2009 | |
| 47 | Brian Zubia | .3950 | 2008-2015 | |
| 49 | Matt Beard | .3962 | 2000-2013 | |
| 50 | Fred Muse | .3963 | 2000-2012 | |
| 51 | Andy McCullough | .3982 | 2000-2014 | |
| 52 | Jon Caruso | .3992 | 2004-2013 | |
| 53 | Jonathan Lung | .3998 | 2000-2011 | |
| 54 | Alan Sweet | .4022 | 2000-2009 | |
| 55 | Gerardo Lozano | .4038 | 2014-2021 | |
| 56 | Morgan Thompson | .4070 | 2005-2014 | |
| 57 | Dan Hagen | .4079 | 2002-2013 | |
| 58 | Chris Auger | .4088 | 2000-2009 | |
| 59 | Matt Taub | .4089 | 2005-2016 | |
| 60 | Jim Patrick | .4094 | 2000-2011 | |
| 61 | Markus Mensink | .4101 | 2000-2008 | |
| 62 | Dave Vilca | .4122 | 2000-2007 | |
| 63 | Mike Henken | .4129 | 2001-2011 | |
| 64 | Logan Johns | .4145 | 2002-2011 | |
| 65 | Will Moore | .4170 | 2000-2009 | |
| 66 | Matt McPeak | .4178 | 2000-2006 | |
| 67 | Ian Starcher | .4213 | 2000-2012 | |
| 68 | Brad Parish | .4214 | 2000-2008 | |
| 69 | Bruce Hernandez | .4232 | 2000-2008 | |
| 70 | Sean Prevost | .4273 | 2005-2014 |
