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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | E | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Roberto Medina# | 26 | 2032-2037 | |
| 2 | Jeff Bane# | 9 | 2025-2031 | |
| 3 | Juan Carlos Cruz# | 7 | 2032-2038 |
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| * Indicates Hall of Fame, # indicates active Player | ||||||||||||||||||||
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| Thursday, June 11th, 2020 - OOTP Baseball 20.8 Build 74 |