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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Blake Asplin# | .667 | 2039-2041 | |
| 1 | Alex Cole# | .667 | 2039-2041 | |
| 1 | Hector Fernandez# | .667 | 2039-2041 |
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| * Indicates Hall of Fame, # indicates active Player | ||||||||||||||||||||
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| Tuesday, April 2nd , 2024 - OOTP Baseball 23.10 Build 110 |