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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Career Leaderboard |
|---|---|---|---|---|
| 1 | Kyle Zimmer | .846 | 2016 | |
| 2 | Wil Crowe# | .800 | 2020 | |
| 2 | Brady Feigl# | .800 | 2022 | |
| 4 | Evan McKendry# | .789 | 2024 | |
| 5 | Trevor Bauer | .786 | 2014 | |
| 5 | Jacob Turner | .786 | 2017 | |
| 7 | Alex Cook# | .765 | 2025 | |
| 8 | Blake Treinen# | .762 | 2014 | |
| 9 | Andre Jackson# | .750 | 2023 | |
| 9 | Carlos Pimentel | .750 | 2017 | |
| 11 | Blake Treinen# | .737 | 2015 | |
| 11 | Thomas Szapucki# | .737 | 2021 | |
| 13 | Ryan Garcia# | .733 | 2022 | |
| 13 | Nathan Wiles# | .733 | 2023 | |
| 13 | Connor Thomas# | .733 | 2022 | |
| 13 | Steven Zobac# | .733 | 2025 | |
| 17 | Danny Rosenbaum | .722 | 2015 | |
| 18 | Alec Marsh# | .706 | 2023 | |
| 18 | R.J. Alaniz | .706 | 2014 | |
| 20 | Deck McGuire | .700 | 2017 | |
| 21 | Sean Nolin | .692 | 2015 | |
| 22 | Matthew Tracy | .688 | 2017 | |
| 23 | Matthew Boyd# | .684 | 2017 | |
| 23 | Aaron West | .684 | 2016 | |
| 25 | Steven Johnson | .682 | 2013 | |
| 25 | Shane Carle | .682 | 2017 | |
| 27 | Steven Wright | .650 | 2021 | |
| 28 | Brody McCullough# | .647 | 2025 | |
| 28 | Trystan Vrieling# | .647 | 2025 | |
| 30 | Ricky Knapp | .643 | 2018 | |
| 31 | Jeff Criswell# | .636 | 2025 | |
| 32 | Carlos Contreras | .619 | 2015 | |
| 33 | Jordan Yamamoto# | .615 | 2022 | |
| 34 | Trevor Bauer | .609 | 2013 | |
| 34 | Jake Faria# | .609 | 2016 | |
| 36 | Cade Horton# | .600 | 2024 | |
| 36 | Blake Bivens | .600 | 2019 | |
| 36 | Carlos Contreras | .600 | 2014 | |
| 36 | Jason Hursh | .600 | 2016 | |
| 40 | Mark Sappington | .591 | 2015 | |
| 41 | Felix Jorge | .588 | 2021 | |
| 41 | Brent Honeywell Jr.# | .588 | 2017 | |
| 43 | Kyle Tyler# | .579 | 2024 | |
| 43 | Ariel Miranda | .579 | 2019 | |
| 45 | Jon Heasley# | .571 | 2023 | |
| 45 | Genesis Cabrera# | .571 | 2021 | |
| 47 | Sean Nolin | .565 | 2014 | |
| 48 | Andrew Wantz# | .556 | 2020 | |
| 48 | Logan Workman# | .556 | 2024 | |
| 48 | Deck McGuire | .556 | 2015 | |
| 48 | Brett Graves | .556 | 2020 | |
| 52 | Kyle McGowin# | .550 | 2021 | |
| 53 | William Roberts | .545 | 2017 | |
| 54 | Jack Leiter# | .538 | 2023 | |
| 55 | Phil Irwin | .533 | 2013 | |
| 55 | Danny Rosenbaum | .533 | 2014 | |
| 55 | Jack Wynkoop | .533 | 2021 | |
| 55 | Robert Dugger | .533 | 2018 | |
| 59 | Edwin Diaz# | .529 | 2016 | |
| 59 | A.J. Puckett# | .529 | 2019 | |
| 61 | Devin Jones | .526 | 2015 | |
| 61 | Alec Hansen | .526 | 2021 | |
| 61 | Percy Garner | .526 | 2016 | |
| 64 | Bowden Francis# | .524 | 2021 | |
| 64 | Matthew Lujan | .524 | 2017 | |
| 64 | Andrew Wantz# | .524 | 2021 | |
| 67 | Jason Hursh | .520 | 2015 | |
| 68 | Henry Sosa | .500 | 2013 | |
| 68 | George Soriano# | .500 | 2023 | |
| 68 | Misael Siverio | .500 | 2016 | |
| 68 | Nick Nastrini# | .500 | 2024 | |
| 68 | Caleb Cotham | .500 | 2015 | |
| 68 | Simon Castro | .500 | 2015 | |
| 68 | Ty Madden# | .500 | 2024 | |
| 68 | Logan Allen# | .500 | 2020 | |
| 68 | Taylor Hill | .500 | 2014 | |
| 68 | Chris Gloor | .500 | 2014 | |
| 68 | Stevie Emanuels# | .500 | 2024 | |
| 68 | Drew Harrington | .500 | 2021 | |
| 68 | Tommy Milone | .500 | 2019 | |
| 68 | Christian Friedrich | .500 | 2019 | |
| 68 | Devin Smeltzer# | .500 | 2021 | |
| 68 | Roansy Contreras# | .500 | 2025 | |
| 68 | Brandon Birdsell# | .500 | 2024 | |
| 85 | Raul Alcantara# | .476 | 2017 | |
| 85 | Christian Bergman | .476 | 2014 | |
| 87 | Ian Oxnevad | .474 | 2021 | |
| 87 | Henry Sosa | .474 | 2014 | |
| 87 | Marcus Walden | .474 | 2014 | |
| 90 | Austin Bibens-Dirkx | .471 | 2014 | |
| 90 | Mason Barnett# | .471 | 2024 | |
| 90 | Aaron Brooks | .471 | 2018 | |
| 93 | Kevin P. Smith | .467 | 2020 | |
| 94 | Nathan Bannister | .450 | 2018 | |
| 94 | Nabil Crismatt# | .450 | 2017 | |
| 96 | Emmett Olson# | .444 | 2025 | |
| 96 | Cody Poteet# | .444 | 2018 | |
| 98 | Tommy Milone | .438 | 2020 | |
| 98 | Chris O'Grady | .438 | 2017 | |
| 100 | Xzavion Curry# | .435 | 2022 |
