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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Avery Parkinson | .3227 | 2007-2011 | |
| 2 | Ernesto Molina | .3272 | 2013-2016 | |
| 3 | Toby Ayers# | .3298 | 2019-2022 | |
| 4 | Walter Daniel | .3361 | 2017-2020 | |
| 5 | Chris Patterson | .3396 | 2007-2011 | |
| 6 | Jonah Martin | .4234 | 2009-2012 |
