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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Postseason Career Leaderboard |
|---|---|---|---|---|
| 1 | Matt Purke | .2000 | 2015 | |
| 2 | Jose Urena# | .2469 | 2014 | |
| 3 | Chris Dwyer | .2973 | 2014 | |
| 4 | Dillon Peters# | .3000 | 2023 | |
| 5 | Jackson Stephens# | .3375 | 2015 | |
| 6 | Jimmy Gillheeney | .3636 | 2013 | |
| 6 | Branden Kline | .3636 | 2016 | |
| 8 | Eric Hacker | .3766 | 2021 | |
| 9 | Matt Canterino# | .3768 | 2021 | |
| 10 | Colin Rodgers | .3824 | 2015 | |
| 11 | James Marvel | .3944 | 2021 | |
| 12 | Tyler Rogers# | .3966 | 2016 | |
| 13 | Conor Harber | .4038 | 2021 | |
| 14 | Giovanni Soto | .4127 | 2014 | |
| 15 | Sam Bachman# | .4219 | 2023 | |
| 16 | Chad Kuhl# | .4462 | 2024 |
