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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | DP | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Fletcher Caldwell# | 6 | 2034-2036 | |
| 2 | Bill Becker | 3 | 2030-2032 | |
| 2 | Rodrigo Flores | 3 | 2031-2033 |
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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 |