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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Gus Kawilarang# | .667 | 2101-2107 | |
| 1 | Yen-ti Yo# | .667 | 2101-2107 | |
| 3 | Jing Szema# | .333 | 2102-2107 |
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| * Indicates Hall of Fame, # indicates active Player | ||||||||||||||||||||
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| Monday, October 23rd , 2023 - OOTP Baseball 24.10 Build 82 |