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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Postseason Career Leaderboard |
|---|---|---|---|---|
| 1 | Luke Hamlin# | 1.000 | 2000 | |
| 2 | Roger Pavlik# | .500 | 2000 |
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| * Indicates Hall of Fame, # indicates active Player | |||||||||||||||
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| Saturday, July 12th , 2025 - OOTP Baseball 26.5 Build 66 |