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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Michael McCarthy | .3874 | 2013-2017 | |
| 2 | Ivan Pineyro | .4063 | 2014-2019 |
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| * Indicates Hall of Fame, # indicates active Player | |||||||||||||||
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| Tuesday, September 30th , 2025 - OOTP Baseball 26.7 Build 77 |