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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | DP | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Juan Jimínez# | 2 | 2028-2030 | |
| 2 | John Clayton# | 0 | 2021-2023 |
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| * Indicates Hall of Fame, # indicates active Player | |||||||||||||||
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| Sunday, March 18th, 2018 - OOTP Baseball 18.8 Build 76 |