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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | DP | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Silas Roby# | 4 | 1886-1890 | |
| 2 | Harry Leavitt# | 1 | 1886-1890 | |
| 2 | Irving Sullivan# | 1 | 1886-1890 |
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| * Indicates Hall of Fame, # indicates active Player | ||||||||||||||||||||
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| Monday, March 30th , 2026 - OOTP Baseball 27.1 Build 50 |