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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | PO | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Dave Young# | 273 | 2016-2025 | |
| 2 | Nelson Plasenia# | 207 | 2017-2028 | |
| 3 | Iván Chacón# | 139 | 2024-2027 |
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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 |