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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Career Leaderboard |
|---|---|---|---|---|
| 1 | Billy Bishop# | .2813 | 2022 | |
| 2 | Jud Graham# | .2828 | 2017 | |
| 3 | Austin Malinowski# | .2852 | 2016 | |
| 4 | Kyle Rogers# | .2885 | 2020 | |
| 5 | Sean Hjelle# | .2892 | 2020 | |
| 6 | Robert Gasser# | .2918 | 2023 | |
| 7 | Lawrence Taylor# | .2964 | 2017 | |
| 8 | Harry Richardson# | .2981 | 2018 | |
| 9 | Sixto Sanchez# | .3034 | 2020 | |
| 10 | Michael Torretta# | .3106 | 2018 | |
| 11 | Billy Bishop# | .3130 | 2020 | |
| 12 | Alex Early# | .3255 | 2022 | |
| 13 | Ray Harris | .3259 | 2014 | |
| 14 | Mason Denaburg# | .3286 | 2020 | |
| 15 | Edward Small# | .3290 | 2017 | |
| 16 | Alex Early# | .3308 | 2023 | |
| 17 | Calvin Welch# | .3315 | 2019 | |
| 18 | Kyle Rogers# | .3383 | 2021 | |
| 19 | Rich Beasley# | .3388 | 2019 | |
| 20 | Ken Waldichuk# | .3405 | 2021 | |
| 21 | Alvin Tigner# | .3419 | 2023 | |
| 22 | Tony Gutiérrez# | .3473 | 2020 | |
| 23 | Reid Detmers# | .3478 | 2021 | |
| 24 | Drew Rom# | .3489 | 2023 | |
| 25 | Tate Rodemaker# | .3493 | 2023 | |
| 26 | Julio Robina# | .3502 | 2023 | |
| 27 | Mason Denaburg# | .3538 | 2019 | |
| 28 | Cy Young, IV# | .3548 | 2022 | |
| 29 | Jack Kochanowicz# | .3552 | 2021 | |
| 30 | Kyle Zimmer | .3571 | 2014 | |
| 31 | Billy Bishop# | .3580 | 2021 | |
| 32 | Jack Kochanowicz# | .3601 | 2023 | |
| 33 | Wes Clark# | .3602 | 2019 | |
| 34 | Ken Gary# | .3604 | 2018 | |
| 35 | Ryan Sims# | .3606 | 2021 | |
| 36 | Esteban Vázquez# | .3608 | 2020 | |
| 37 | Danny William# | .3611 | 2017 | |
| 37 | Carlos Martínez# | .3611 | 2023 | |
| 39 | Nick Robison# | .3620 | 2016 | |
| 40 | Carlos García | .3628 | 2015 | |
| 41 | Eduardo Rodriguez# | .3643 | 2015 | |
| 42 | James Marinan# | .3657 | 2022 | |
| 43 | Ryan Sims# | .3695 | 2022 | |
| 44 | Justin Collop | .3710 | 2012 | |
| 45 | Tahnaj Thomas# | .3714 | 2021 | |
| 46 | Billy Bishop# | .3716 | 2019 | |
| 47 | Juan Romero# | .3720 | 2014 | |
| 48 | Alex Meyer | .3758 | 2012 | |
| 49 | T.J. Sikkema# | .3763 | 2022 | |
| 50 | Maverick Kingsburry# | .3778 | 2022 | |
| 51 | Jorge Flores# | .3786 | 2019 | |
| 52 | Robert Hayes | .3806 | 2019 | |
| 53 | Víctor De La Rosa | .3807 | 2014 | |
| 54 | Bobby Simmons# | .3812 | 2023 | |
| 55 | Peter Solomon# | .3819 | 2019 | |
| 56 | Skylar Spurrier# | .3843 | 2021 | |
| 57 | Nathan Armstrong# | .3923 | 2022 | |
| 58 | Doug Nikhazy# | .3943 | 2023 | |
| 59 | Jason McCracken# | .3990 | 2014 | |
| 60 | Anthony Klumpp# | .4049 | 2018 | |
| 61 | Matt Parker# | .4164 | 2020 | |
| 61 | J.D. Shockley# | .4164 | 2020 | |
| 63 | Domingo Tapia | .4171 | 2013 | |
| 64 | William Cuevas | .4184 | 2014 | |
| 65 | José Ortega# | .4216 | 2021 | |
| 66 | Don Day# | .4283 | 2017 | |
| 67 | Carlos Pimentel | .4288 | 2013 | |
| 68 | Jeff Wiley | .4301 | 2017 | |
| 69 | Will Inman | .4309 | 2012 | |
| 70 | Patrick Wischusen# | .4317 | 2023 | |
| 71 | Richard White# | .4321 | 2013 | |
| 72 | Nino Guillaume# | .4333 | 2018 | |
| 73 | Don Day# | .4413 | 2018 | |
| 74 | Mason Radeke# | .4548 | 2013 | |
| 75 | Hideaki Hirose# | .4825 | 2013 |
