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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | E | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Curt Carey# | 2 | 2020-2021 | |
| 2 | Corey Rearick# | 1 | 2020-2021 | |
| 2 | Zack Rottman# | 1 | 2020-2021 |
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| * Indicates Hall of Fame, # indicates active Player | ||||||||||||||||||||
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| Monday, January 6th , 2025 - OOTP Baseball 25.11 Build 101 |