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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | E | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Fernando Rodríguez# | 6 | 2025-2027 | |
| 2 | Juan Carlos Cruz# | 5 | 2022-2024 |
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| * Indicates Hall of Fame, # indicates active Player | |||||||||||||||
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| Monday, September 18th, 2017 - OOTP Baseball 18.7 Build 74 |