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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | A | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | José Silva# | 18 | 2021-2029 | |
| 2 | António Montés | 15 | 2020-2024 |
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| * Indicates Hall of Fame, # indicates active Player | |||||||||||||||
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| Tuesday, June 12th, 2018 - OOTP Baseball 18.8 Build 76 |