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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | David Buchanan# | .4036 | 2013-2023 | |
| 2 | Brett Kerry# | .4296 | 2022-2025 | |
| 3 | Casey Kelly# | .4405 | 2017-2024 | |
| 4 | Eric Hacker | .4467 | 2016-2020 | |
| 5 | Justin Dunn# | .4513 | 2018-2026 | |
| 6 | William Cuevas# | .4514 | 2016-2026 | |
| 7 | Ryan Carpenter# | .4695 | 2013-2023 | |
| 8 | Logan Darnell | .4701 | 2014-2023 |
