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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Luis Leyva | .2540 | 2013-2019 | |
| 2 | Will Lester | .2571 | 2021-2023 | |
| 3 | Júlio Caraballo | .2602 | 2030-2034 | |
| 4 | Dave Boyer# | .2621 | 2043-2051 | |
| 5 | Toby Adams | .3277 | 2034-2047 | |
| 6 | Rory Taverner | .3487 | 2023-2025 | |
| 7 | Takeichi Koike | .3630 | 2017-2020 | |
| 8 | Bill Davis | .3758 | 2030-2037 | |
| 8 | Jarred Benson | .3758 | 2038-2043 | |
| 10 | Bubba McCall# | .3833 | 2046-2051 | |
| 11 | Michael Calhoun | .3846 | 2044-2049 |
