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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Brandon Dickson | .3535 | 2010-2012 | |
| 2 | Ryan Feierabend | .3600 | 2007-2014 | |
| 3 | Nathan Eovaldi# | .3704 | 2013-2015 | |
| 4 | Casey Crosby | .3922 | 2013-2016 | |
| 5 | Eduardo Rodriguez# | .3940 | 2014-2018 | |
| 6 | Lucas Harrell | .4034 | 2013-2018 | |
| 7 | Michael Mariot# | .4202 | 2016-2023 | |
| 8 | Clayton Richard | .4238 | 2013-2017 | |
| 9 | Rob Scahill | .4318 | 2013-2019 | |
| 10 | Felix Doubront | .4331 | 2016-2019 | |
| 11 | Deolis Guerra | .4336 | 2013-2022 | |
| 12 | Simon Castro | .4405 | 2013-2020 | |
| 13 | Scott Diamond | .4428 | 2013-2021 | |
| 14 | Brent Honeywell Jr.# | .4450 | 2018-2020 | |
| 15 | Allen Webster | .4468 | 2013-2021 | |
| 16 | Brandon Cumpton | .4502 | 2014-2019 | |
| 17 | Brad Mills | .4519 | 2013-2017 | |
| 18 | Braden Shipley# | .4527 | 2017-2023 | |
| 19 | Bernardo Flores# | .4585 | 2021-2023 | |
| 20 | Caleb Smith# | .4594 | 2017-2023 | |
| 21 | Brett Kennedy# | .4649 | 2019-2023 | |
| 22 | Burch Smith# | .4661 | 2016-2022 | |
| 23 | Luke Weaver# | .4691 | 2017-2023 | |
| 24 | Mitch White# | .4703 | 2019-2023 | |
| 25 | Brent Suter# | .4714 | 2017-2023 | |
| 26 | Kolby Allard# | .4746 | 2018-2021 | |
| 27 | Brooks Raley# | .4763 | 2014-2020 | |
| 28 | John Gast | .4771 | 2013-2017 | |
| 29 | Ryan Merritt# | .4792 | 2016-2023 | |
| 30 | Casey Coleman# | .4816 | 2013-2023 | |
| 31 | Brooks Hall# | .4836 | 2015-2023 | |
| 32 | Brock Stewart# | .4873 | 2017-2023 | |
| 33 | Mike Wright# | .4888 | 2015-2023 | |
| 34 | Tommy Milone# | .4918 | 2016-2023 | |
| 35 | Brandon Leibrandt# | .5039 | 2018-2023 | |
| 36 | Dillon Overton | .5223 | 2016-2022 | |
| 37 | Paolo Espino | .5554 | 2016-2023 |
