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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Postseason Career Leaderboard |
|---|---|---|---|---|
| 1 | Dakota Hudson# | .1000 | 2021 | |
| 2 | Garrett Hill# | .1429 | 2025 | |
| 3 | Sammy Solis | .2254 | 2015 | |
| 4 | Zachary Nuding | .2687 | 2013 | |
| 5 | Carl Edwards Jr.# | .2754 | 2015 | |
| 6 | Ryan Carpenter# | .3134 | 2021 | |
| 7 | Pierce Johnson# | .3143 | 2015 | |
| 8 | Kyle McPherson | .3158 | 2016 | |
| 9 | Blade Tidwell# | .3175 | 2024 | |
| 10 | Henry Owens | .3448 | 2014 | |
| 11 | Clayton Blackburn | .3538 | 2015 | |
| 12 | Sam Bachman# | .3559 | 2024 | |
| 13 | Dario Agrazal# | .3710 | 2021 | |
| 14 | Drew Rucinski# | .3770 | 2024 | |
| 15 | Marcus Stroman# | .3846 | 2014 | |
| 16 | Tyler Thornburg | .3893 | 2013 | |
| 17 | Logan Darnell | .4217 | 2014 | |
| 18 | Ryan Yarbrough# | .4306 | 2017 | |
| 19 | Matt Grimes | .4706 | 2018 | |
| 20 | Tanner Gordon# | .4853 | 2023 | |
| 21 | Michael Kopech# | .4918 | 2018 | |
| 22 | Robert Stephenson# | .5000 | 2014 | |
| 23 | Dan Straily | .5132 | 2021 | |
| 24 | Tejay Antone# | .5429 | 2019 | |
| 25 | Scott Snodgress | .5714 | 2013 |
