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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Manuel González | .537 | 2013-2021 | |
| 2 | Jonathan Tobin | .457 | 2010-2019 | |
| 3 | Paul Miller | .357 | 2019-2026 |
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| * Indicates Hall of Fame, # indicates active Player | ||||||||||||||||||||
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| Thursday, June 11th, 2020 - OOTP Baseball 20.8 Build 74 |