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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | ERA | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Gregory Billo | 3.923 | 2015-2020 | |
| 2 | Bob Mathews | 4.438 | 2021-2025 | |
| 3 | Jorge Marrero | 4.777 | 2023-2027 |
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| * Indicates Hall of Fame, # indicates active Player | ||||||||||||||||||||
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| Friday, June 5th, 2020 - OOTP Baseball 21.3 Build 54 |