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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Darin Gillies# | .3269 | 2016-2023 | |
| 2 | Jeff Ames | .3808 | 2014-2017 | |
| 3 | Jake Stinnett | .3982 | 2017-2021 | |
| 4 | Erick Leal | .3986 | 2018-2021 | |
| 5 | Brendon Little# | .4127 | 2018-2022 | |
| 6 | Jordan Pries | .4167 | 2013-2016 | |
| 7 | Max Lazar# | .4265 | 2018-2022 | |
| 8 | Mason Radeke | .4387 | 2014-2018 | |
| 9 | A.J. Ladwig# | .4418 | 2017-2022 | |
| 10 | Ian Clarkin# | .4467 | 2015-2023 | |
| 11 | Jose Taveras | .4686 | 2019-2023 |
