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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | E | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Scott Ramsey# | 11 | 2024-2027 | |
| 2 | Francisco Guerra# | 10 | 2026-2028 |
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| * Indicates Hall of Fame, # indicates active Player | |||||||||||||||
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| Wednesday, September 19th, 2018 - OOTP Baseball 18.8 Build 76 |