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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Chase Johnson | 38 | 2016-2020 | |
| 2 | Joey Murray# | 34 | 2020-2026 | |
| 3 | Osvaldo Hernandez# | 33 | 2020-2025 | |
| 4 | Matt Crouse | 32 | 2014-2016 | |
| 5 | Tyson Perez | 31 | 2014-2017 | |
| 6 | Paul Demny | 30 | 2013-2016 | |
| 7 | Kevin Eichhorn | 29 | 2014-2018 | |
| 8 | Alex Burgos | 28 | 2013-2015 | |
| 8 | Thomas Lee | 28 | 2014-2023 | |
| 8 | Drew Strotman# | 28 | 2018-2024 | |
| 11 | Casey Bloomquist | 27 | 2016-2022 | |
| 12 | Jorgan Cavanerio | 26 | 2017-2022 | |
| 13 | Kyle Johnston | 25 | 2019-2022 | |
| 13 | Zach McCambley# | 25 | 2022-2024 | |
| 13 | Joe Navilhon | 25 | 2020-2023 | |
| 13 | James Needy | 25 | 2017-2019 | |
| 17 | Sean Brady | 24 | 2019-2021 | |
| 17 | Oscar De La Cruz | 24 | 2016-2019 | |
| 17 | Tyler Higgins | 24 | 2016-2020 | |
| 17 | Patrick Urckfitz | 24 | 2015-2017 | |
| 21 | Franklyn Kilome# | 23 | 2020-2024 | |
| 22 | Ronald Herrera# | 22 | 2019-2024 | |
| 22 | Jordan Minch | 22 | 2018-2021 | |
| 24 | Gray Fenter | 21 | 2017-2024 | |
| 24 | Jairo Heredia | 21 | 2014-2018 | |
| 24 | Jake Wong# | 21 | 2020-2024 | |
| 24 | Gabriel Ynoa | 21 | 2015-2021 | |
| 28 | Andrew Alvarez# | 20 | 2024-2025 | |
| 28 | Endrys Briceno | 20 | 2014-2019 | |
| 28 | Brandon Eisert# | 20 | 2020-2026 | |
| 28 | Clay Helvey# | 20 | 2020-2025 | |
| 28 | Hector Perez# | 20 | 2017-2026 | |
| 28 | Chad Smith | 20 | 2013-2016 | |
| 34 | Adrian Chaidez# | 19 | 2023-2026 | |
| 34 | Daniel Gil | 19 | 2013-2016 | |
| 34 | Sam Runion | 19 | 2013-2016 | |
| 34 | Edwin Uceta# | 19 | 2020-2021 | |
| 34 | Boone Whiting | 19 | 2013-2014 | |
| 39 | Jaime Barria# | 18 | 2019-2020 | |
| 39 | Austin Bizzle | 18 | 2018-2023 | |
| 39 | Sean Donatello | 18 | 2014-2016 | |
| 39 | Jacob Esch | 18 | 2014-2017 | |
| 39 | Jorge Guzman# | 18 | 2018-2024 | |
| 39 | Rainy Lara | 18 | 2015-2016 | |
| 39 | Michael Lorenzen# | 18 | 2014-2015 | |
| 39 | Chris Perry | 18 | 2014-2017 | |
| 39 | Aldo Ramirez# | 18 | 2022-2025 | |
| 39 | Michael Roth | 18 | 2013-2019 | |
| 39 | John Swanda# | 18 | 2020-2026 | |
| 39 | Corey Walter | 18 | 2018-2021 | |
| 51 | Bryan Baker# | 17 | 2018-2022 | |
| 51 | Ryan Bradley | 17 | 2013-2016 | |
| 51 | Ben Krauth | 17 | 2019-2023 | |
| 51 | Ryan Longstreth | 17 | 2015-2017 | |
| 51 | Nick Maronde | 17 | 2013-2017 | |
| 51 | Nick Mikolajchak# | 17 | 2021-2025 | |
| 51 | Chris Pike | 17 | 2016-2018 | |
| 51 | Julian Smith# | 17 | 2022-2025 | |
| 51 | Tom Windle | 17 | 2014-2022 | |
| 51 | Kyle Zimmer | 17 | 2015-2021 | |
| 61 | Peyton Battenfield# | 16 | 2022-2024 | |
| 61 | Tyler Brown# | 16 | 2022-2024 | |
| 61 | Josh Dye# | 16 | 2020-2025 | |
| 61 | Chris Flexen# | 16 | 2017-2017 | |
| 61 | Ryan Helsley# | 16 | 2017-2018 | |
| 61 | Griff McGarry# | 16 | 2023-2025 | |
| 61 | Jordan Montgomery# | 16 | 2017-2017 | |
| 61 | Alan Rangel# | 16 | 2019-2021 | |
| 61 | John Stilson | 16 | 2013-2018 | |
| 61 | Kelvin Vasquez | 16 | 2015-2021 | |
| 61 | Angel Yepez | 16 | 2018-2021 | |
| 72 | D.J. Baxendale | 15 | 2014-2015 | |
| 72 | Parker Bridwell | 15 | 2014-2022 | |
| 72 | Duncan Davitt# | 15 | 2025-2026 | |
| 72 | Edgar De La Rosa | 15 | 2014-2017 | |
| 72 | Jhonathan Diaz# | 15 | 2019-2026 | |
| 72 | Hunter Dobbins# | 15 | 2023-2024 | |
| 72 | Jeff Ferrell | 15 | 2014-2015 | |
| 72 | Justin Garza# | 15 | 2017-2021 | |
| 72 | Sean Harney# | 15 | 2024-2026 | |
| 72 | Nick Hernandez# | 15 | 2018-2023 | |
| 72 | Gunnar Hoglund# | 15 | 2022-2024 | |
| 72 | Jackson Kowar# | 15 | 2020-2021 | |
| 72 | Kevin Matthews | 15 | 2014-2016 | |
| 72 | T.J. McFarland | 15 | 2017-2018 | |
| 72 | Willy Paredes | 15 | 2014-2016 | |
| 72 | Ivan Pineyro | 15 | 2014-2022 | |
| 72 | Michael Plassmeyer# | 15 | 2020-2021 | |
| 72 | Thomas Ponticelli | 15 | 2022-2024 | |
| 72 | Armando Rivero | 15 | 2015-2017 | |
| 72 | Nivaldo Rodriguez# | 15 | 2021-2026 | |
| 72 | Joe Ross# | 15 | 2014-2015 | |
| 72 | Austin Sodders | 15 | 2019-2021 | |
| 72 | Eric Stout# | 15 | 2018-2026 | |
| 72 | Eric Wooten | 15 | 2017-2017 | |
| 96 | Xavier Altamirano | 14 | 2019-2022 | |
| 96 | Jeremy Bleich | 14 | 2013-2018 | |
| 96 | Damon Casetta-Stubbs# | 14 | 2021-2026 | |
| 96 | Henry Centeno | 14 | 2017-2021 | |
| 96 | Christian Cosby# | 14 | 2022-2025 |
