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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | E | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | José Flores | 20 | 2018-2027 | |
| 2 | Luis Hernández | 16 | 2021-2030 | |
| 3 | Ray Davis# | 15 | 2016-2031 |
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| * Indicates Hall of Fame, # indicates active Player | ||||||||||||||||||||
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| Tuesday, June 12th, 2018 - OOTP Baseball 18.8 Build 76 |