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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Postseason Career Leaderboard |
|---|---|---|---|---|
| 1 | Roger Stewart# | .0893 | 2029 | |
| 2 | Manuel García | .1636 | 2020 | |
| 3 | Rubén Cabrera# | .3143 | 2023 | |
| 4 | Bob Moore | .3231 | 2014 | |
| 5 | Richard Lawson# | .4648 | 2023 |
