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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Juan Pérez | .543 | 2017-2023 | |
| 2 | Lance de Valk | .493 | 2025-2030 | |
| 3 | Pat Hunt | .472 | 2017-2029 |
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| * Indicates Hall of Fame, # indicates active Player | ||||||||||||||||||||
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| Friday, March 26th, 2021 - OOTP Baseball 20.8 Build 74 |