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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | E | YEAR | Open Career Leaderboard |
|---|---|---|---|---|
| 1 | Osiris Johnson# | 9 | 2024 | |
| 2 | Jeremy Rodriguez# | 8 | 2024 | |
| 3 | Frederick Bencosme# | 7 | 2024 | |
| 4 | Jamari Baylor | 5 | 2024 |
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| * Indicates Hall of Fame, # indicates active Player | |||||||||||||||||||||||||
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| Friday, May 23rd , 2025 - OOTP Baseball 26.3 Build 55 |