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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Erick Leal | .745 | 2018-2021 | |
| 2 | Mason Radeke | .532 | 2014-2018 | |
| 3 | Jeff Ames | .514 | 2014-2017 |
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| * Indicates Hall of Fame, # indicates active Player | ||||||||||||||||||||
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| Tuesday, April 15th , 2025 - OOTP Baseball 26.2 Build 50 |