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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | DP | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | António Montés# | 3 | 2020-2024 | |
| 2 | José Silva# | 2 | 2021-2028 |
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| * Indicates Hall of Fame, # indicates active Player | |||||||||||||||
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| Monday, September 18th, 2017 - OOTP Baseball 18.7 Build 74 |