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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Carlos Rodon# | .714 | 2016-2019 | |
| 2 | Miguel A. Gonzalez | .333 | 2014-2018 |
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| * Indicates Hall of Fame, # indicates active Player | |||||||||||||||
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| Friday, August 15th , 2025 - OOTP Baseball 26.6 Build 73 |