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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Fred Humphrey | .5465 | 1984-1988 | |
| 2 | Carl Meyers | .4286 | 1997-2000 |
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| * Indicates Hall of Fame, # indicates active Player | |||||||||||||||
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| Sunday, August 17th, 2014 - OOTP Baseball 15.5 Build 25 |