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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | DP | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Rand McNally# | 3 | 2030-2034 | |
| 1 | Mike Russell | 3 | 2021-2025 | |
| 3 | Tim Waters# | 2 | 2026-2033 |
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| * Indicates Hall of Fame, # indicates active Player | ||||||||||||||||||||
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| Friday, March 29th, 2019 - OOTP Baseball 18.8 Build 76 |