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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Sherwood Aguilar | .2528 | 1993-1997 | |
| 2 | Francisco Silva# | .2888 | 2007-2012 | |
| 3 | Júlio López | .3003 | 2005-2012 | |
| 4 | Santiago Cruz | .3185 | 1971-1976 | |
| 5 | John Spens | .3260 | 1973-1979 | |
| 6 | Stu Ellis | .3293 | 1972-1976 | |
| 7 | Jorge Encarnación | .3512 | 1968-1974 | |
| 8 | Kazuhiro Ono | .3551 | 1968-1981 | |
| 9 | Emílio Vásquez | .3577 | 1961-1965 | |
| 10 | Darren Smith# | .3657 | 2006-2012 | |
| 11 | Gerald May# | .3729 | 2008-2015 | |
| 12 | Stephen Jones# | .4065 | 2009-2015 | |
| 13 | David Lamparello# | .4120 | 2007-2014 | |
| 14 | Peter Simpson# | .4164 | 2008-2015 |
