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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Jamie Conway# | 1.000 | 2037-2047 | |
| 2 | Bill Williams# | .667 | 2045-2047 |
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| * Indicates Hall of Fame, # indicates active Player | |||||||||||||||
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| Tuesday, July 22nd , 2025 - OOTP Baseball 25.11 Build 104 |