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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | E | YEAR | Open Career Leaderboard |
|---|---|---|---|---|
| 1 | Dan Sims# | 6 | 2048 | |
| 2 | Hector Garcia# | 4 | 2048 | |
| 2 | Kevin Bale# | 4 | 2048 | |
| 4 | Brian Matthews# | 3 | 2048 |
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| * Indicates Hall of Fame, # indicates active Player | |||||||||||||||||||||||||
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| Monday, September 15th , 2025 - OOTP Baseball 26.7 Build 77 |