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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | PCT | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Cosmo Bjorkenheim# | .995 | 2025-2029 | |
| 2 | Luis Antonio Hernández | .983 | 2016-2025 |
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| * Indicates Hall of Fame, # indicates active Player | |||||||||||||||
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| Friday, July 19th, 2019 - OOTP Baseball 20.5 Build 52 |