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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Christian Bergman | 43 | 2014-2019 | |
| 2 | Deck McGuire | 40 | 2014-2019 | |
| 3 | Jason Hursh | 34 | 2014-2020 | |
| 3 | Kyle T. Smith | 34 | 2016-2024 | |
| 5 | Matt Dermody# | 33 | 2017-2024 | |
| 5 | Blake Treinen# | 33 | 2014-2016 | |
| 7 | Carlos Contreras | 32 | 2014-2017 | |
| 8 | Taylor Hill | 31 | 2014-2018 | |
| 8 | Steven Johnson | 31 | 2013-2017 | |
| 10 | Jordan Stephens | 30 | 2019-2024 | |
| 11 | Austin Bibens-Dirkx | 28 | 2014-2018 | |
| 11 | Danny Rosenbaum | 28 | 2013-2015 | |
| 13 | Severino Gonzalez | 27 | 2014-2019 | |
| 14 | Jason Garcia | 26 | 2015-2020 | |
| 14 | Sean Nolin | 26 | 2013-2015 | |
| 16 | Trevor Bauer | 25 | 2013-2014 | |
| 16 | Austin Cox# | 25 | 2020-2025 | |
| 16 | Jake Kalish# | 25 | 2018-2024 | |
| 16 | Adam Seminaris# | 25 | 2023-2025 | |
| 16 | Touki Toussaint# | 25 | 2018-2025 | |
| 21 | Jeff Bain# | 24 | 2019-2025 | |
| 21 | Peyton Battenfield# | 24 | 2022-2025 | |
| 21 | Jake Faria# | 24 | 2016-2025 | |
| 24 | Chris Gloor | 23 | 2013-2016 | |
| 24 | Alec Marsh# | 23 | 2022-2024 | |
| 24 | Carlos Pimentel | 23 | 2014-2017 | |
| 24 | A.J. Puckett# | 23 | 2017-2025 | |
| 24 | Henry Sosa | 23 | 2013-2016 | |
| 24 | Jordan Yamamoto# | 23 | 2016-2023 | |
| 30 | Garrett Cleavinger# | 22 | 2017-2022 | |
| 30 | Tommy Milone | 22 | 2018-2020 | |
| 30 | Thomas Szapucki# | 22 | 2018-2022 | |
| 30 | Matthew Tomshaw | 22 | 2016-2021 | |
| 30 | Matthew Tracy | 22 | 2016-2019 | |
| 30 | Marcus Walden | 22 | 2014-2022 | |
| 36 | Simon Castro | 21 | 2013-2016 | |
| 36 | Brady Feigl# | 21 | 2019-2025 | |
| 36 | Corbin Martin# | 21 | 2019-2026 | |
| 36 | Hector Perez# | 21 | 2019-2025 | |
| 36 | Andrew Wantz# | 21 | 2020-2021 | |
| 41 | Edgar Arredondo# | 20 | 2019-2025 | |
| 41 | Nabil Crismatt# | 20 | 2017-2026 | |
| 41 | Jon Heasley# | 20 | 2022-2023 | |
| 41 | Evan McKendry# | 20 | 2022-2026 | |
| 41 | Matt Pierpont | 20 | 2017-2021 | |
| 41 | Aaron West | 20 | 2013-2017 | |
| 47 | Jason Adam# | 19 | 2015-2022 | |
| 47 | Jacob Bray | 19 | 2019-2022 | |
| 47 | Genesis Cabrera# | 19 | 2019-2021 | |
| 47 | Kevin Herget# | 19 | 2017-2021 | |
| 47 | Gregory Infante | 19 | 2013-2017 | |
| 47 | Kyle Lobstein | 19 | 2017-2020 | |
| 47 | Kevin McCarthy | 19 | 2015-2022 | |
| 47 | Andrew Perez# | 19 | 2022-2025 | |
| 47 | Cody Reed | 19 | 2017-2020 | |
| 47 | William Roberts | 19 | 2015-2017 | |
| 47 | Forrest Snow | 19 | 2015-2019 | |
| 58 | Maximo Castillo# | 18 | 2022-2026 | |
| 58 | Johan Dominguez# | 18 | 2023-2025 | |
| 58 | Andrew Faulkner | 18 | 2014-2021 | |
| 58 | Percy Garner | 18 | 2014-2016 | |
| 58 | Phillipp Klein | 18 | 2014-2017 | |
| 58 | Reiss Knehr# | 18 | 2021-2026 | |
| 58 | Luis Patino# | 18 | 2024-2026 | |
| 58 | Riley Pint# | 18 | 2018-2026 | |
| 58 | Adam Stauffer# | 18 | 2023-2026 | |
| 58 | Jameson Taillon# | 18 | 2013-2014 | |
| 58 | Connor Thomas# | 18 | 2022-2026 | |
| 58 | Colton Turner | 18 | 2017-2021 | |
| 58 | Edwin Uceta# | 18 | 2022-2026 | |
| 58 | Collin Wiles# | 18 | 2020-2025 | |
| 58 | Steven Wright | 18 | 2013-2021 | |
| 73 | Matthew Bowman# | 17 | 2014-2021 | |
| 73 | Aaron Brooks | 17 | 2016-2019 | |
| 73 | Bowden Francis# | 17 | 2020-2022 | |
| 73 | Alec Hansen | 17 | 2019-2021 | |
| 73 | Jackson Kowar# | 17 | 2020-2026 | |
| 73 | Cole Sands# | 17 | 2022-2023 | |
| 73 | Jesse Scholtens# | 17 | 2020-2025 | |
| 73 | Cody Sedlock# | 17 | 2022-2025 | |
| 73 | Carson Seymour# | 17 | 2023-2026 | |
| 73 | Greg Smith | 17 | 2013-2016 | |
| 73 | Garrett Stallings# | 17 | 2022-2025 | |
| 73 | Jacob Turner | 17 | 2017-2020 | |
| 73 | Adam Wilk | 17 | 2013-2019 | |
| 86 | R.J. Alaniz | 16 | 2014-2022 | |
| 86 | Edwin Fierro | 16 | 2018-2022 | |
| 86 | Jack Leiter# | 16 | 2022-2025 | |
| 86 | Tyson Miller# | 16 | 2020-2022 | |
| 86 | Brian Moran# | 16 | 2013-2024 | |
| 86 | Jayden Murray# | 16 | 2023-2026 | |
| 86 | Chris O'Grady | 16 | 2017-2020 | |
| 86 | Sean O'Sullivan | 16 | 2014-2018 | |
| 86 | Andy Oliver | 16 | 2013-2018 | |
| 86 | Tom Robson | 16 | 2014-2020 | |
| 86 | Angel Rondon# | 16 | 2022-2026 | |
| 86 | Mark Sappington | 16 | 2015-2017 | |
| 86 | Misael Siverio | 16 | 2016-2018 | |
| 86 | Matt Tabor# | 16 | 2023-2025 | |
| 86 | Josh Taylor# | 16 | 2017-2022 |
