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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Jeff Bittiger | .3068 | 1993-2002 | |
| 2 | Joel Kirsten | .3222 | 2006-2011 | |
| 3 | Derek Blacksher | .3340 | 2009-2014 | |
| 4 | Tim Brown | .3496 | 2009-2017 | |
| 5 | Ben Moore | .3499 | 2008-2014 | |
| 6 | Kyle Ruwe | .3531 | 2006-2014 | |
| 7 | Chris Rodgers | .3842 | 2088-2094 | |
| 8 | Alex Boshers | .3919 | 2015-2065 | |
| 9 | Richard Salazar | .3999 | 2008-2013 | |
| 10 | Will Davis | .4017 | 2091-2096 | |
| 11 | Jon Morrow | .4070 | 2067-2076 | |
| 12 | Hector Segui | .4084 | 2088-2096 | |
| 13 | Gil Wozniak | .4161 | 2086-2097 | |
| 14 | Victor Espinoza# | .4202 | 2093-2098 | |
| 15 | Steven Estes | .4348 | 2083-2095 |
