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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Branden Kline | .3952 | 2014-2016 | |
| 2 | Conor Harber | .4148 | 2016-2021 | |
| 3 | Eric Hacker | .4767 | 2017-2022 | |
| 4 | Chad Kuhl# | .5130 | 2023-2025 |
