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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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| Sunday, March 15th , 2026 - OOTP Baseball 27.1 Build 42 |