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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | E | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | John Clayton# | 14 | 2021-2023 | |
| 2 | Jin-yong Myung# | 5 | 2030-2032 | |
| 3 | Juan Jimínez# | 3 | 2028-2031 |
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| * Indicates Hall of Fame, # indicates active Player | ||||||||||||||||||||
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| Saturday, December 22nd, 2018 - OOTP Baseball 18.8 Build 76 |