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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 | Osvaldo Hernandez# | 33 | 2020-2025 | |
| 3 | Matt Crouse | 32 | 2014-2016 | |
| 4 | Tyson Perez | 31 | 2014-2017 | |
| 5 | Paul Demny | 30 | 2013-2016 | |
| 6 | Kevin Eichhorn | 29 | 2014-2018 | |
| 7 | Alex Burgos | 28 | 2013-2015 | |
| 7 | Thomas Lee | 28 | 2014-2023 | |
| 7 | Drew Strotman# | 28 | 2018-2024 | |
| 10 | Casey Bloomquist | 27 | 2016-2022 | |
| 11 | Jorgan Cavanerio | 26 | 2017-2022 | |
| 11 | Joey Murray# | 26 | 2020-2024 | |
| 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 | Endrys Briceno | 20 | 2014-2019 | |
| 28 | Brandon Eisert# | 20 | 2020-2022 | |
| 28 | Clay Helvey# | 20 | 2020-2025 | |
| 28 | Chad Smith | 20 | 2013-2016 | |
| 32 | Andrew Alvarez# | 19 | 2024-2025 | |
| 32 | Daniel Gil | 19 | 2013-2016 | |
| 32 | Sam Runion | 19 | 2013-2016 | |
| 32 | Edwin Uceta# | 19 | 2020-2021 | |
| 32 | Boone Whiting | 19 | 2013-2014 | |
| 37 | Jaime Barria# | 18 | 2019-2020 | |
| 37 | Austin Bizzle | 18 | 2018-2023 | |
| 37 | Sean Donatello | 18 | 2014-2016 | |
| 37 | Jacob Esch | 18 | 2014-2017 | |
| 37 | Jorge Guzman# | 18 | 2018-2024 | |
| 37 | Rainy Lara | 18 | 2015-2016 | |
| 37 | Michael Lorenzen# | 18 | 2014-2015 | |
| 37 | Chris Perry | 18 | 2014-2017 | |
| 37 | Aldo Ramirez# | 18 | 2022-2025 | |
| 37 | Michael Roth | 18 | 2013-2019 | |
| 37 | Corey Walter | 18 | 2018-2021 | |
| 48 | Bryan Baker# | 17 | 2018-2022 | |
| 48 | Ryan Bradley | 17 | 2013-2016 | |
| 48 | Ben Krauth | 17 | 2019-2023 | |
| 48 | Ryan Longstreth | 17 | 2015-2017 | |
| 48 | Nick Maronde | 17 | 2013-2017 | |
| 48 | Hector Perez# | 17 | 2017-2025 | |
| 48 | Chris Pike | 17 | 2016-2018 | |
| 48 | John Swanda# | 17 | 2020-2025 | |
| 48 | Tom Windle | 17 | 2014-2022 | |
| 48 | Kyle Zimmer | 17 | 2015-2021 | |
| 58 | Peyton Battenfield# | 16 | 2022-2024 | |
| 58 | Tyler Brown# | 16 | 2022-2024 | |
| 58 | Chris Flexen# | 16 | 2017-2017 | |
| 58 | Ryan Helsley# | 16 | 2017-2018 | |
| 58 | Nick Mikolajchak# | 16 | 2021-2025 | |
| 58 | Jordan Montgomery# | 16 | 2017-2017 | |
| 58 | Alan Rangel# | 16 | 2019-2021 | |
| 58 | John Stilson | 16 | 2013-2018 | |
| 58 | Kelvin Vasquez | 16 | 2015-2021 | |
| 58 | Angel Yepez | 16 | 2018-2021 | |
| 68 | D.J. Baxendale | 15 | 2014-2015 | |
| 68 | Parker Bridwell | 15 | 2014-2022 | |
| 68 | Edgar De La Rosa | 15 | 2014-2017 | |
| 68 | Hunter Dobbins# | 15 | 2023-2024 | |
| 68 | Jeff Ferrell | 15 | 2014-2015 | |
| 68 | Justin Garza# | 15 | 2017-2021 | |
| 68 | Nick Hernandez# | 15 | 2018-2023 | |
| 68 | Gunnar Hoglund# | 15 | 2022-2024 | |
| 68 | Jackson Kowar# | 15 | 2020-2021 | |
| 68 | Kevin Matthews | 15 | 2014-2016 | |
| 68 | T.J. McFarland | 15 | 2017-2018 | |
| 68 | Griff McGarry# | 15 | 2023-2025 | |
| 68 | Willy Paredes | 15 | 2014-2016 | |
| 68 | Ivan Pineyro | 15 | 2014-2022 | |
| 68 | Michael Plassmeyer# | 15 | 2020-2021 | |
| 68 | Thomas Ponticelli | 15 | 2022-2024 | |
| 68 | Armando Rivero | 15 | 2015-2017 | |
| 68 | Joe Ross# | 15 | 2014-2015 | |
| 68 | Julian Smith# | 15 | 2022-2025 | |
| 68 | Austin Sodders | 15 | 2019-2021 | |
| 68 | Eric Wooten | 15 | 2017-2017 | |
| 89 | Xavier Altamirano | 14 | 2019-2022 | |
| 89 | Jeremy Bleich | 14 | 2013-2018 | |
| 89 | Damon Casetta-Stubbs# | 14 | 2021-2025 | |
| 89 | Henry Centeno | 14 | 2017-2021 | |
| 89 | Christian Cosby# | 14 | 2022-2025 | |
| 89 | Jackson Goddard# | 14 | 2020-2025 | |
| 89 | Myles Jaye | 14 | 2013-2015 | |
| 89 | Trey Jeans | 14 | 2021-2023 | |
| 89 | Brandon G. Koch# | 14 | 2019-2024 | |
| 89 | Casey Legumina# | 14 | 2020-2024 | |
| 89 | Brendon Little# | 14 | 2018-2024 | |
| 89 | Seth Lugo# | 14 | 2015-2016 |
