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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Career Leaderboard |
|---|---|---|---|---|
| 1 | Carl Edwards Jr.# | .3361 | 2015 | |
| 2 | Charlie Barnes# | .3610 | 2022 | |
| 3 | Michael Kopech# | .3627 | 2018 | |
| 4 | Brad Bergesen | .3628 | 2015 | |
| 5 | David Buchanan# | .3656 | 2022 | |
| 6 | Brad Peacock | .3672 | 2016 | |
| 7 | Miguel Celestino | .3777 | 2015 | |
| 8 | Marcus Stroman# | .3794 | 2014 | |
| 9 | Drew Rucinski# | .3846 | 2024 | |
| 9 | Brett Kerry# | .3846 | 2024 | |
| 11 | Odrisamer Despaigne# | .3855 | 2023 | |
| 12 | Cody Martin | .3866 | 2013 | |
| 13 | Brad Bergesen | .3880 | 2014 | |
| 14 | Tim Melville | .3888 | 2015 | |
| 15 | Casey Kelly# | .3950 | 2022 | |
| 16 | Adalberto Mejia | .3971 | 2017 | |
| 17 | Mark Appel | .3979 | 2015 | |
| 18 | Austin Pruitt# | .4000 | 2017 | |
| 18 | Brady Lail | .4000 | 2016 | |
| 20 | Odrisamer Despaigne# | .4006 | 2022 | |
| 21 | Dylan Axelrod | .4013 | 2014 | |
| 22 | Ryan Carpenter# | .4019 | 2021 | |
| 23 | Tim Melville | .4045 | 2014 | |
| 24 | William Cuevas# | .4058 | 2023 | |
| 25 | Rob Whalen | .4062 | 2016 | |
| 26 | Ryan Dennick | .4082 | 2015 | |
| 27 | David Buchanan# | .4083 | 2023 | |
| 28 | Colin Rea# | .4095 | 2021 | |
| 29 | Mason Adams# | .4111 | 2025 | |
| 30 | Williams Perez | .4125 | 2021 | |
| 31 | Nick Travieso | .4192 | 2015 | |
| 32 | Marcelo Martinez# | .4224 | 2023 | |
| 33 | Casey Kelly# | .4226 | 2024 | |
| 34 | Jacob Turner | .4266 | 2014 | |
| 35 | Steven Wright | .4286 | 2015 | |
| 36 | Sam Gaviglio | .4288 | 2017 | |
| 37 | Zachary Nuding | .4294 | 2013 | |
| 38 | Eric Hacker | .4301 | 2020 | |
| 39 | Casey Kelly# | .4311 | 2023 | |
| 39 | Jack Patterson | .4311 | 2021 | |
| 41 | Zac Lowther# | .4350 | 2023 | |
| 42 | Drew Rucinski# | .4378 | 2021 | |
| 43 | Mikey O'Brien | .4382 | 2015 | |
| 44 | Robbie Erlin# | .4395 | 2017 | |
| 45 | David Festa# | .4398 | 2024 | |
| 46 | Aaron Thompson | .4399 | 2013 | |
| 47 | Barret Loux | .4424 | 2016 | |
| 48 | Eric Hacker | .4450 | 2016 | |
| 49 | Jacob Nix# | .4460 | 2023 | |
| 50 | Mark Appel | .4473 | 2016 | |
| 50 | Kyle Lobstein | .4473 | 2013 | |
| 52 | Mario Hollands | .4488 | 2016 | |
| 53 | Tejay Antone# | .4517 | 2024 | |
| 54 | Luis Madero# | .4538 | 2023 | |
| 55 | Ariel Pena | .4558 | 2015 | |
| 56 | Brett Kerry# | .4573 | 2022 | |
| 57 | Ryan Rolison# | .4611 | 2024 | |
| 58 | Ryan Carpenter# | .4620 | 2022 | |
| 59 | Jakob Junis# | .4634 | 2017 | |
| 60 | Justin Dunn# | .4647 | 2024 | |
| 61 | Luis Madero# | .4655 | 2022 | |
| 62 | Logan Darnell | .4670 | 2015 | |
| 63 | Zech Lemond | .4684 | 2017 | |
| 64 | Eric Hacker | .4718 | 2018 | |
| 65 | James McArthur# | .4725 | 2023 | |
| 66 | Orangel Arenas | .4741 | 2015 | |
| 67 | William Cuevas# | .4825 | 2024 | |
| 68 | Ryan Carpenter# | .4919 | 2023 | |
| 69 | Justin Nicolino | .5222 | 2015 |
