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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | E | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Anthony Trujillo | 10 | 2016-2024 | |
| 2 | Iikka Karpinen# | 8 | 2030-2034 |
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| * Indicates Hall of Fame, # indicates active Player | |||||||||||||||
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| Friday, March 29th, 2019 - OOTP Baseball 18.8 Build 76 |