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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | DP | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Cosmo Bjorkenheim# | 2 | 2025-2029 | |
| 1 | Luis Antonio Hernández# | 2 | 2016-2025 |
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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 |