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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | William Cuevas# | 4 | 2016-2024 | |
| 1 | Eric Hacker | 4 | 2016-2020 | |
| 1 | Tyler Thornburg | 4 | 2013-2014 | |
| 4 | Clayton Blackburn | 3 | 2015-2018 | |
| 4 | Ryan Carpenter# | 3 | 2013-2023 | |
| 4 | Yonardo Herdenez | 3 | 2019-2022 | |
| 4 | Trevor Kelley# | 3 | 2018-2024 | |
| 4 | Adalberto Mejia | 3 | 2015-2017 | |
| 4 | Ryan Yarbrough# | 3 | 2017-2020 | |
| 10 | Tim Alderson | 2 | 2014-2016 | |
| 10 | Sam Bachman# | 2 | 2024-2025 | |
| 10 | Brian Clark | 2 | 2017-2021 | |
| 10 | Logan Darnell | 2 | 2014-2023 | |
| 10 | Odrisamer Despaigne# | 2 | 2021-2023 | |
| 10 | Justin Donatella | 2 | 2019-2023 | |
| 10 | Carl Edwards Jr.# | 2 | 2015-2016 | |
| 10 | Tyler Glasnow# | 2 | 2016-2021 | |
| 10 | Dakota Hudson# | 2 | 2019-2021 | |
| 10 | Mauricio Llovera# | 2 | 2020-2024 | |
| 10 | Kyle McPherson | 2 | 2016-2016 | |
| 10 | Patrick Murphy# | 2 | 2022-2023 | |
| 10 | Zachary Nuding | 2 | 2013-2015 | |
| 10 | Riley O'Brien# | 2 | 2021-2024 | |
| 10 | Henry Owens | 2 | 2014-2014 | |
| 10 | Dylan TeBrake# | 2 | 2024-2024 | |
| 26 | Andury Acevedo | 1 | 2015-2019 | |
| 26 | Dario Agrazal# | 1 | 2019-2024 | |
| 26 | Scott Alexander# | 1 | 2014-2015 | |
| 26 | Xavier Altamirano | 1 | 2019-2021 | |
| 26 | Tejay Antone# | 1 | 2018-2024 | |
| 26 | Mark Appel | 1 | 2015-2018 | |
| 26 | Dylan Axelrod | 1 | 2014-2014 | |
| 26 | Luke Bard | 1 | 2015-2021 | |
| 26 | Scott Barlow# | 1 | 2019-2019 | |
| 26 | Tyler Beede# | 1 | 2017-2017 | |
| 26 | Jesse Biddle | 1 | 2014-2020 | |
| 26 | Nolan Blackwood# | 1 | 2019-2023 | |
| 26 | Jeremy Bleich | 1 | 2013-2021 | |
| 26 | Lisalberto Bonilla | 1 | 2013-2016 | |
| 26 | Michael Brady | 1 | 2014-2017 | |
| 26 | Sam Bragg | 1 | 2018-2018 | |
| 26 | David Buchanan# | 1 | 2013-2023 | |
| 26 | Walker Buehler# | 1 | 2018-2020 | |
| 26 | Gerardo Carrillo# | 1 | 2023-2024 | |
| 26 | Will Carter | 1 | 2021-2022 | |
| 26 | Henry Centeno | 1 | 2016-2019 | |
| 26 | Preston Claiborne | 1 | 2013-2016 | |
| 26 | Trevor Clifton# | 1 | 2016-2019 | |
| 26 | Dylan Covey# | 1 | 2017-2023 | |
| 26 | Matt Custred | 1 | 2018-2019 | |
| 26 | Indigo Diaz# | 1 | 2024-2024 | |
| 26 | Jonathan Dziedzic | 1 | 2018-2020 | |
| 26 | Mason Englert# | 1 | 2023-2024 | |
| 26 | Tyler Ferguson# | 1 | 2016-2016 | |
| 26 | David Festa# | 1 | 2024-2024 | |
| 26 | Charlie Furbush | 1 | 2018-2021 | |
| 26 | Juan Gonzalez | 1 | 2016-2021 | |
| 26 | John Gorman | 1 | 2016-2020 | |
| 26 | Matthew Grace | 1 | 2018-2020 | |
| 26 | Matt Grimes | 1 | 2018-2018 | |
| 26 | Lincoln Henzman# | 1 | 2021-2023 | |
| 26 | Jay Jackson# | 1 | 2016-2020 | |
| 26 | Justin Jarvis# | 1 | 2023-2023 | |
| 26 | Erik Johnson | 1 | 2013-2014 | |
| 26 | Jakob Junis# | 1 | 2017-2017 | |
| 26 | Casey Kelly# | 1 | 2017-2024 | |
| 26 | Evan Kravetz# | 1 | 2022-2024 | |
| 26 | Bobby LaFromboise | 1 | 2017-2017 | |
| 26 | Jonathan Loaisiga# | 1 | 2018-2020 | |
| 26 | Aaron Loup | 1 | 2013-2021 | |
| 26 | Wyatt Marks | 1 | 2019-2020 | |
| 26 | Phil Maton# | 1 | 2017-2021 | |
| 26 | Mason McCullough | 1 | 2017-2021 | |
| 26 | Brian Miller | 1 | 2019-2020 | |
| 26 | James Naile# | 1 | 2018-2024 | |
| 26 | Freddy Peralta# | 1 | 2017-2018 | |
| 26 | Konnor Pilkington# | 1 | 2020-2024 | |
| 26 | Benino Pruneda | 1 | 2016-2018 | |
| 26 | Matt Purke | 1 | 2013-2017 | |
| 26 | Reid Redman | 1 | 2018-2018 | |
| 26 | Jesus Reyes | 1 | 2021-2023 | |
| 26 | Esmil Rogers | 1 | 2014-2014 | |
| 26 | Drew Rucinski# | 1 | 2021-2024 | |
| 26 | Jaime Schultz | 1 | 2017-2018 | |
| 26 | Tarik Skubal# | 1 | 2020-2021 | |
| 26 | Sammy Solis | 1 | 2015-2015 | |
| 26 | Gabe Speier# | 1 | 2018-2023 | |
| 26 | Robert Stephenson# | 1 | 2014-2017 | |
| 26 | Dan Straily | 1 | 2013-2021 | |
| 26 | Cody Stull | 1 | 2018-2020 | |
| 26 | Joander Suarez# | 1 | 2024-2025 | |
| 26 | John Swanda# | 1 | 2022-2022 | |
| 26 | Stephen Tarpley# | 1 | 2020-2024 | |
| 26 | Aaron Thompson | 1 | 2013-2015 | |
| 26 | Zach Thornton | 1 | 2016-2017 | |
| 26 | Carlos Torres | 1 | 2013-2021 | |
| 26 | Christian Torres | 1 | 2018-2018 | |
| 26 | Corey Walter | 1 | 2017-2020 | |
| 26 | Brad Wieck# | 1 | 2021-2023 | |
| 26 | Nick Wittgren# | 1 | 2014-2015 |
