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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Robert Osborne | .2455 | 2014-2020 | |
| 2 | Willi Kehr | .2846 | 2026-2028 | |
| 3 | Jim Shaffner | .3097 | 2039-2042 | |
| 4 | Neil Millirons | .3148 | 2038-2040 | |
| 5 | Felipe Arreola | .3165 | 2027-2028 | |
| 6 | Ánibal Altichioro | .3246 | 2024-2028 | |
| 7 | Blake Mastromarino | .3387 | 2045-2048 | |
| 8 | Juan Martínez | .4035 | 2028-2029 | |
| 9 | Victor Vicente# | .4348 | 2048-2053 | |
| 10 | Jake Robinson | .4407 | 2017-2024 | |
| 11 | John Haslam# | .4468 | 2057-2060 | |
| 12 | Steve Atkins# | .4603 | 2059-2060 | |
| 13 | Clay Tedesco# | .5036 | 2056-2058 |
