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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | DP | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Jim Burch# | 22 | 2025-2030 | |
| 2 | Júlio Mateo# | 18 | 2023-2027 | |
| 3 | Dennis Clifton | 14 | 2021-2028 |
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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 |