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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Carl Edwards Jr.# | .2544 | 2015-2016 | |
| 2 | Ryan Carpenter# | .3878 | 2013-2023 | |
| 3 | Tyler Thornburg | .4056 | 2013-2014 | |
| 4 | Eric Hacker | .4467 | 2016-2020 | |
| 5 | William Cuevas# | .4649 | 2016-2026 | |
| 6 | Tejay Antone# | .5417 | 2018-2024 |
