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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Career Leaderboard |
|---|---|---|---|---|
| 1 | Nathan Eovaldi# | .882 | 2013 | |
| 2 | Brant Hurter# | .812 | 2024 | |
| 3 | Trevor Cahill | .800 | 2016 | |
| 4 | Eduardo Rodriguez# | .789 | 2016 | |
| 5 | Jack Flaherty# | .769 | 2018 | |
| 5 | Brent Suter# | .769 | 2020 | |
| 7 | Clayton Richard | .765 | 2017 | |
| 8 | Drew Hutchison# | .762 | 2022 | |
| 9 | Osvaldo Bido# | .750 | 2024 | |
| 9 | Brent Honeywell Jr.# | .750 | 2018 | |
| 11 | Brian Matusz | .737 | 2013 | |
| 11 | Brandon Cumpton | .737 | 2015 | |
| 11 | Tsuyoshi Wada | .737 | 2013 | |
| 14 | Robert Gasser# | .733 | 2024 | |
| 14 | Brock Burke# | .733 | 2022 | |
| 16 | Brett Cecil | .727 | 2013 | |
| 16 | Nathan Eovaldi# | .727 | 2014 | |
| 18 | Rich Hill# | .722 | 2024 | |
| 18 | Simon Castro | .722 | 2013 | |
| 20 | Brett Kennedy# | .714 | 2020 | |
| 21 | Brian Flynn | .706 | 2016 | |
| 21 | Vladimir Gutierrez# | .706 | 2021 | |
| 23 | Chase Silseth# | .700 | 2025 | |
| 24 | Rob Kaminsky | .696 | 2022 | |
| 25 | Randy Vasquez# | .692 | 2024 | |
| 26 | Angel Rondon# | .688 | 2025 | |
| 26 | Felix Doubront | .688 | 2018 | |
| 28 | Dylan File# | .684 | 2023 | |
| 28 | Josh Tomlin | .684 | 2014 | |
| 30 | Tanner Bibee# | .682 | 2023 | |
| 31 | Brock Stewart# | .667 | 2020 | |
| 31 | Rubby de la Rosa# | .667 | 2014 | |
| 31 | Gerrit Cole# | .667 | 2014 | |
| 31 | Kenny Rosenberg# | .667 | 2025 | |
| 31 | Brandon Leibrandt# | .667 | 2022 | |
| 36 | Corey Kluber | .652 | 2014 | |
| 37 | Wes Parsons | .650 | 2021 | |
| 37 | Trevor Rogers# | .650 | 2025 | |
| 39 | Bubba Chandler# | .647 | 2025 | |
| 39 | Blaine Hardy | .647 | 2020 | |
| 41 | Kolby Allard# | .643 | 2021 | |
| 42 | Ben Lively# | .632 | 2024 | |
| 42 | David Hess | .632 | 2022 | |
| 42 | Alex Cobb# | .632 | 2013 | |
| 42 | Brent Honeywell Jr.# | .632 | 2020 | |
| 46 | Scott Diamond | .625 | 2015 | |
| 46 | Kwang-hyun Kim# | .625 | 2025 | |
| 48 | John Ely | .619 | 2015 | |
| 48 | Dillon Overton | .619 | 2022 | |
| 50 | Humberto Mejia# | .611 | 2023 | |
| 50 | Nabil Crismatt# | .611 | 2021 | |
| 50 | Scott Diamond | .611 | 2014 | |
| 50 | Colton Gordon# | .611 | 2024 | |
| 50 | Paolo Espino# | .611 | 2017 | |
| 50 | Eduardo Rodriguez# | .611 | 2017 | |
| 50 | Brandon Workman | .611 | 2017 | |
| 50 | Zac Lowther# | .611 | 2021 | |
| 58 | Jesse Scholtens# | .609 | 2022 | |
| 58 | Bryan Woo# | .609 | 2024 | |
| 60 | Alfredo Simon | .600 | 2014 | |
| 60 | Chris Martin# | .600 | 2015 | |
| 60 | Tyler Wilson | .600 | 2017 | |
| 60 | August Schlosser | .600 | 2015 | |
| 60 | Nicholas Kingham | .600 | 2015 | |
| 60 | Reid Detmers# | .600 | 2023 | |
| 66 | Collin Wiles# | .591 | 2023 | |
| 66 | Jacob Nix# | .591 | 2022 | |
| 68 | Clayton Beeter# | .588 | 2025 | |
| 68 | Edward Cabrera# | .588 | 2024 | |
| 68 | Tyler Alexander# | .588 | 2023 | |
| 68 | Juan Nicasio | .588 | 2013 | |
| 72 | Lucas Harrell | .583 | 2015 | |
| 73 | Brandon Dickson | .579 | 2010 | |
| 73 | Allen Webster | .579 | 2014 | |
| 73 | Gabriel Ynoa | .579 | 2017 | |
| 73 | Dylan Dodd# | .579 | 2023 | |
| 73 | Kyle McPherson | .579 | 2015 | |
| 78 | Jesse Scholtens# | .571 | 2023 | |
| 78 | Nicholas Kingham | .571 | 2014 | |
| 78 | Nathan Eovaldi# | .571 | 2015 | |
| 81 | Lucas Harrell | .565 | 2013 | |
| 81 | Mitch White# | .565 | 2023 | |
| 81 | Brent Honeywell Jr.# | .565 | 2019 | |
| 84 | Clayton Richard | .562 | 2016 | |
| 84 | Tyler Alexander# | .562 | 2024 | |
| 84 | Jose De Leon# | .562 | 2017 | |
| 84 | Dillon Overton | .562 | 2018 | |
| 88 | Jose Alvarez | .556 | 2014 | |
| 88 | Sixto Sanchez# | .556 | 2025 | |
| 88 | Jordan Lyles# | .556 | 2017 | |
| 88 | Joey Murray# | .556 | 2025 | |
| 92 | Scott Blewett# | .550 | 2018 | |
| 92 | Kolby Allard# | .550 | 2019 | |
| 94 | John Gast | .545 | 2014 | |
| 94 | Jameson Taillon# | .545 | 2015 | |
| 94 | Manny Banuelos# | .545 | 2014 | |
| 94 | Tsuyoshi Wada | .545 | 2014 | |
| 94 | Tyler Anderson# | .545 | 2015 | |
| 99 | Bryan Hudson# | .538 | 2022 | |
| 100 | Burch Smith | .533 | 2020 |
