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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Jeremy Beasley# | .4327 | 2020-2026 | |
| 2 | Adam Morgan | .4367 | 2013-2023 | |
| 3 | Adonis Medina# | .4692 | 2019-2025 |
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| * Indicates Hall of Fame, # indicates active Player | ||||||||||||||||||||
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| Friday, October 2nd , 2026 - OOTP Baseball 27.4 Build 76 |