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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Byron Chad# | .667 | 2060-2062 | |
| 2 | Rachmad Subadio# | .500 | 2060-2062 | |
| 3 | Moges Odoyo# | .250 | 2060-2062 |
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| * Indicates Hall of Fame, # indicates active Player | ||||||||||||||||||||
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| Wednesday, May 14th , 2025 - OOTP Baseball 26.2 Build 50 |