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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Ryan Feierabend | .3600 | 2007-2014 | |
| 2 | Nathan Eovaldi# | .3704 | 2013-2015 | |
| 3 | Lucas Harrell | .4034 | 2013-2018 | |
| 4 | Clayton Richard | .4238 | 2013-2017 | |
| 5 | Rob Scahill | .4318 | 2013-2019 | |
| 6 | Felix Doubront | .4331 | 2016-2019 | |
| 7 | Osvaldo Bido# | .4385 | 2022-2026 | |
| 8 | Jose De Leon# | .4418 | 2017-2025 | |
| 9 | Scott Diamond | .4428 | 2013-2021 | |
| 10 | Brent Honeywell Jr.# | .4450 | 2018-2020 | |
| 11 | Kwang-hyun Kim# | .4454 | 2023-2026 | |
| 12 | Allen Webster | .4468 | 2013-2021 | |
| 13 | Brandon Cumpton | .4502 | 2014-2019 | |
| 14 | Brad Mills | .4519 | 2013-2017 | |
| 15 | Braden Shipley | .4556 | 2017-2024 | |
| 16 | Humberto Mejia# | .4637 | 2022-2025 | |
| 17 | Brett Kennedy# | .4649 | 2019-2023 | |
| 18 | Burch Smith | .4661 | 2016-2022 | |
| 19 | Luke Weaver# | .4669 | 2017-2024 | |
| 20 | Mitch White# | .4703 | 2019-2023 | |
| 21 | Brooks Raley# | .4735 | 2014-2024 | |
| 22 | Kolby Allard# | .4746 | 2018-2021 | |
| 23 | Ross Detwiler | .4817 | 2014-2024 | |
| 24 | Mike Wright | .4936 | 2015-2024 | |
| 25 | Brandon Leibrandt# | .5032 | 2018-2025 | |
| 26 | Dillon Overton | .5223 | 2016-2022 | |
| 27 | Paolo Espino# | .5442 | 2016-2025 |
