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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Postseason Career Leaderboard |
|---|---|---|---|---|
| 1 | Maximo Castillo# | .2917 | 2023 | |
| 2 | David Peterson# | .2951 | 2020 | |
| 3 | Rubby de la Rosa# | .2987 | 2014 | |
| 4 | Corbin Martin# | .3000 | 2019 | |
| 5 | Kwang-hyun Kim# | .3077 | 2025 | |
| 6 | Tobias Myers# | .3115 | 2024 | |
| 7 | Brian Flynn | .3200 | 2014 | |
| 8 | Jack Patterson | .3333 | 2020 | |
| 8 | John Gast | .3333 | 2017 | |
| 8 | Tyler Alexander# | .3333 | 2024 | |
| 11 | Brett Cecil | .3535 | 2013 | |
| 12 | Paolo Espino# | .3714 | 2017 | |
| 13 | Gabriel Ynoa | .3762 | 2017 | |
| 14 | Jordan Lyles# | .3770 | 2017 | |
| 15 | Randall Delgado | .3846 | 2013 | |
| 16 | Brent Honeywell Jr.# | .3913 | 2019 | |
| 17 | Jose Alvarez | .4000 | 2014 | |
| 18 | Manny Banuelos# | .4026 | 2014 | |
| 19 | Alex Cobb# | .4043 | 2013 | |
| 20 | Luke Weaver# | .4177 | 2021 | |
| 21 | Mike Vinson | .4219 | 2016 | |
| 22 | Osvaldo Bido# | .4225 | 2024 | |
| 23 | T.J. House | .4368 | 2017 | |
| 24 | Nathan Eovaldi# | .4483 | 2013 | |
| 25 | Jakob Junis# | .4487 | 2024 | |
| 26 | Brian Matusz | .4521 | 2013 | |
| 27 | Jack Flaherty# | .4545 | 2018 | |
| 28 | Trevor Rogers# | .4730 | 2025 | |
| 29 | Jesse Biddle | .4769 | 2015 | |
| 30 | Collin Wiles# | .4861 | 2023 | |
| 31 | Brooks Raley# | .5000 | 2016 | |
| 31 | Austen Williams | .5000 | 2020 | |
| 31 | Emerson Hancock# | .5000 | 2023 | |
| 34 | Brady Rodgers | .5070 | 2017 | |
| 35 | Nicholas Kingham | .5143 | 2015 | |
| 36 | Cody Morris# | .5606 | 2023 | |
| 37 | Nick Travieso | .5735 | 2016 | |
| 38 | Jarred Cosart | .6000 | 2013 |
