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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | A | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Zac Veen# | 9 | 2021-2024 | |
| 2 | Stone Garrett# | 2 | 2021-2024 | |
| 2 | Johnathan Rodriguez# | 2 | 2024-2024 |
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| * Indicates Hall of Fame, # indicates active Player | ||||||||||||||||||||
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| Friday, May 23rd , 2025 - OOTP Baseball 26.3 Build 55 |