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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Chase Johnson | .603 | 2016-2020 | |
| 2 | Thomas Lee | .500 | 2014-2023 | |
| 3 | Jorgan Cavanerio | .426 | 2017-2022 |
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| * Indicates Hall of Fame, # indicates active Player | ||||||||||||||||||||
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| Tuesday, September 30th , 2025 - OOTP Baseball 26.7 Build 77 |