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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Lucas Giolito# | .600 | 2013-2015 | |
| 2 | Diomenges Almengo# | .500 | 2016-2025 | |
| 3 | Chih-Wei Hu | .333 | 2014-2015 |
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| * Indicates Hall of Fame, # indicates active Player | ||||||||||||||||||||
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| Tuesday, January 6th , 2026 - OOTP Baseball 26.8 Build 82 |