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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Javier Duque | .3435 | 2055-2063 | |
| 2 | Hunter Wood | .3439 | 2020-2027 | |
| 3 | Mike Stone# | .3442 | 2090-2097 | |
| 4 | Todd Redmond | .3489 | 2009-2017 | |
| 5 | Mike Jaffe | .3574 | 2031-2038 | |
| 6 | Ben Clemons | .3642 | 2085-2092 | |
| 7 | Willie Estrada | .3689 | 2021-2028 | |
| 8 | Harrison Hickey | .3691 | 2041-2052 | |
| 9 | Michael Shawaryn | .3717 | 2018-2027 | |
| 10 | Rob Whalen | .3742 | 2017-2024 | |
| 11 | Matt Hayden | .3751 | 2079-2088 | |
| 12 | Zaire Stamps | .3762 | 2080-2084 | |
| 13 | Aaron Thornton | .3772 | 2040-2052 | |
| 14 | Jose Bautista | .3788 | 2032-2050 | |
| 15 | Eric DiGiovanni | .3819 | 2080-2093 | |
| 16 | Ethan Bailey | .3835 | 2069-2074 | |
| 17 | B.J. Gutierrez# | .3842 | 2088-2096 | |
| 18 | Tim Krupka | .3849 | 2069-2081 | |
| 19 | Danny Zepeda | .3873 | 2065-2076 | |
| 20 | Justin Moye# | .3885 | 2093-2098 | |
| 21 | Kyle Gibson | .3896 | 2010-2023 | |
| 22 | Malik Hill | .3906 | 2056-2063 | |
| 23 | Mario Trujillo# | .3918 | 2089-2098 | |
| 24 | Jaden Jones | .3925 | 2060-2069 | |
| 25 | Ed Wiseman# | .3946 | 2089-2098 | |
| 26 | Jason Young | .3969 | 2039-2046 | |
| 27 | Jonathon Crawford | .3989 | 2017-2027 | |
| 28 | Juan Ruiz | .4017 | 2084-2093 | |
| 29 | Joe King# | .4018 | 2091-2097 | |
| 30 | Mike Daley | .4025 | 2062-2069 | |
| 31 | Sean Butler | .4037 | 2084-2094 | |
| 32 | Lance Fox | .4038 | 2029-2038 | |
| 33 | Ray Timmons | .4105 | 2072-2079 | |
| 34 | Edgar Gutierrez | .4128 | 2082-2091 | |
| 35 | Tim Murphy | .4304 | 2050-2056 | |
| 36 | Tim Vazquez | .4373 | 2084-2097 | |
| 37 | Ben Kramer | .4395 | 2044-2054 | |
| 38 | Mike Stephenson | .4419 | 2082-2091 |
