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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Josh Hoffman | .3255 | 2010-2014 | |
| 2 | Kyle Chamberlin | .3390 | 2013-2021 | |
| 3 | Gil Johnson | .3509 | 2000-2010 | |
| 4 | Sergio Hernandez | .3528 | 2001-2013 | |
| 5 | Leo Medina | .3531 | 2000-2009 | |
| 6 | Brendan Rees | .3535 | 2001-2010 | |
| 7 | Danny Justice | .3537 | 2000-2010 | |
| 8 | Devin Nisbet | .3590 | 2001-2013 | |
| 9 | Guo Liu | .3720 | 2003-2010 | |
| 10 | Josh Graham | .3728 | 2014-2018 | |
| 11 | Tony Hernandez | .3865 | 2000-2010 | |
| 12 | Jaden Taylor | .3922 | 2005-2013 | |
| 13 | Ryan Iverson | .3940 | 2001-2007 | |
| 14 | Jose Rios | .3942 | 2007-2016 | |
| 15 | Mike Palmer | .3955 | 2000-2010 | |
| 16 | Brian O'Connor | .3976 | 2000-2006 | |
| 17 | Joel Atkinson | .4036 | 2012-2021 | |
| 18 | Phil Goodman | .4039 | 2013-2018 |
