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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | E | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Jeff May# | 3 | 2024-2024 | |
| 2 | Steve Nebeker# | 1 | 2024-2024 | |
| 3 | Kyle Marin# | 0 | 2024-2024 |
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| * Indicates Hall of Fame, # indicates active Player | ||||||||||||||||||||
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| Thursday, October 16th , 2025 - OOTP Baseball 26.7 Build 77 |