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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Chris Reed | .3827 | 2013-2021 | |
| 2 | Bobby Doran | .4140 | 2013-2016 | |
| 3 | Matt Heidenreich | .4166 | 2014-2017 | |
| 4 | Kirk McCarty# | .4212 | 2019-2023 | |
| 5 | Rico Garcia# | .4214 | 2018-2023 | |
| 6 | Matt Gage# | .4302 | 2017-2023 | |
| 7 | Adam Morgan# | .4367 | 2013-2023 | |
| 8 | Dillon McNamara | .4399 | 2018-2021 | |
| 9 | Evan Kruczynski# | .4449 | 2019-2023 | |
| 10 | Eric Jokisch# | .4454 | 2014-2018 | |
| 11 | Dylan Baker | .4487 | 2015-2023 | |
| 12 | Chase De Jong# | .4536 | 2017-2023 | |
| 13 | Julian Merryweather# | .4577 | 2017-2020 | |
| 14 | Adonis Medina# | .4686 | 2019-2023 | |
| 15 | Casey Lawrence | .4886 | 2014-2020 | |
| 16 | Daniel Slania | .5019 | 2017-2021 | |
| 17 | Dalton Sawyer# | .5082 | 2018-2022 |
