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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Jacob Nix# | .3841 | 2016-2024 | |
| 2 | Matt Withrow | .3861 | 2017-2021 | |
| 3 | Yennsy Diaz# | .3972 | 2018-2025 | |
| 4 | Alexis Tapia | .4013 | 2016-2022 | |
| 5 | Roniel Raudes# | .4082 | 2019-2025 | |
| 6 | Nick Travieso | .4152 | 2014-2024 | |
| 7 | Logan Verrett# | .4254 | 2013-2024 | |
| 8 | Jhordany Mezquita# | .4278 | 2021-2025 | |
| 9 | Nicholas Pasquale | .4344 | 2014-2017 | |
| 10 | Reid Birlingmair# | .4350 | 2022-2025 | |
| 11 | Chris Clarke# | .4691 | 2020-2024 |
