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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | E | YEAR | Open Career Leaderboard |
|---|---|---|---|---|
| 1 | Ian Cleary# | 8 | 1962 | |
| 2 | Roger Adair# | 5 | 1962 |
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| * Indicates Hall of Fame, # indicates active Player | |||||||||||||||
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| Friday, January 6th , 2023 - OOTP Baseball 23.10 Build 103 |