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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Rory Taverner | .2483 | 2021-2024 | |
| 2 | Jack Sandford | .2927 | 2031-2034 | |
| 3 | Wynn Thompson | .2949 | 2018-2036 | |
| 4 | David Núñez | .2977 | 2023-2025 | |
| 5 | Carl Bean | .3125 | 2043-2045 | |
| 6 | Jeffrey Gómez | .3701 | 2027-2039 | |
| 7 | Richard Davis | .3723 | 2024-2026 | |
| 8 | Nick Myers# | .3955 | 2044-2045 |
