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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 | Matt Crouse | 32 | 2014-2016 | |
| 3 | Tyson Perez | 31 | 2014-2017 | |
| 4 | Paul Demny | 30 | 2013-2016 | |
| 5 | Kevin Eichhorn | 29 | 2014-2018 | |
| 6 | Alex Burgos | 28 | 2013-2015 | |
| 6 | Thomas Lee# | 28 | 2014-2023 | |
| 8 | Casey Bloomquist | 27 | 2016-2022 | |
| 9 | Jorgan Cavanerio | 26 | 2017-2022 | |
| 10 | Kyle Johnston# | 25 | 2019-2022 | |
| 10 | Joey Murray# | 25 | 2020-2023 | |
| 10 | Joe Navilhon# | 25 | 2020-2023 | |
| 10 | James Needy | 25 | 2017-2019 | |
| 14 | Sean Brady# | 24 | 2019-2021 | |
| 14 | Oscar De La Cruz# | 24 | 2016-2019 | |
| 14 | Tyler Higgins | 24 | 2016-2020 | |
| 14 | Patrick Urckfitz | 24 | 2015-2017 | |
| 18 | Jordan Minch | 22 | 2018-2021 | |
| 18 | Adam Oller# | 22 | 2019-2021 | |
| 20 | Jairo Heredia | 21 | 2014-2018 | |
| 20 | Drew Strotman# | 21 | 2018-2023 | |
| 20 | Jake Wong# | 21 | 2020-2023 | |
| 20 | Gabriel Ynoa | 21 | 2015-2021 | |
| 24 | Endrys Briceno | 20 | 2014-2019 | |
| 24 | Brandon Eisert# | 20 | 2020-2022 | |
| 24 | Osvaldo Hernandez# | 20 | 2020-2023 | |
| 24 | Chad Smith | 20 | 2013-2016 | |
| 28 | Chad Donato# | 19 | 2020-2023 | |
| 28 | Daniel Gil | 19 | 2013-2016 | |
| 28 | Sam Runion | 19 | 2013-2016 | |
| 28 | Edwin Uceta# | 19 | 2020-2021 | |
| 28 | Jaison Vilera# | 19 | 2019-2023 | |
| 28 | Boone Whiting | 19 | 2013-2014 | |
| 34 | Jamie Barria# | 18 | 2019-2020 | |
| 34 | Nick Bennett# | 18 | 2022-2023 | |
| 34 | Austin Bizzle# | 18 | 2018-2023 | |
| 34 | Jose Castillo# | 18 | 2018-2022 | |
| 34 | Sean Donatello | 18 | 2014-2016 | |
| 34 | Jacob Esch | 18 | 2014-2017 | |
| 34 | Jorge Guzman# | 18 | 2018-2023 | |
| 34 | Clay Helvey# | 18 | 2020-2022 | |
| 34 | Rainy Lara | 18 | 2015-2016 | |
| 34 | Michael Lorenzen# | 18 | 2014-2015 | |
| 34 | Francys Peguero# | 18 | 2021-2023 | |
| 34 | Chris Perry | 18 | 2014-2017 | |
| 34 | Paul Richan# | 18 | 2021-2023 | |
| 34 | Michael Roth | 18 | 2013-2019 | |
| 34 | Teddy Stankiewicz | 18 | 2019-2021 | |
| 34 | Corey Walter | 18 | 2018-2021 | |
| 50 | Bryan Baker# | 17 | 2018-2022 | |
| 50 | Matt Bower# | 17 | 2016-2021 | |
| 50 | Ryan Bradley | 17 | 2013-2016 | |
| 50 | Matt Frawley# | 17 | 2018-2023 | |
| 50 | Franklyn Kilome# | 17 | 2020-2021 | |
| 50 | Ben Krauth | 17 | 2019-2023 | |
| 50 | Ryan Longstreth | 17 | 2015-2017 | |
| 50 | Nick Maronde | 17 | 2013-2017 | |
| 50 | Kevin McCanna# | 17 | 2018-2022 | |
| 50 | Chris Pike | 17 | 2016-2018 | |
| 50 | Wei-Chung Wang# | 17 | 2017-2023 | |
| 50 | Tom Windle | 17 | 2014-2022 | |
| 50 | Kyle Zimmer# | 17 | 2015-2021 | |
| 63 | Sandy Baez# | 16 | 2017-2023 | |
| 63 | Chris Flexen# | 16 | 2017-2017 | |
| 63 | Ryan Helsley# | 16 | 2017-2018 | |
| 63 | Jordan Montgomery# | 16 | 2017-2017 | |
| 63 | Alan Rangel# | 16 | 2019-2021 | |
| 63 | John Stilson | 16 | 2013-2018 | |
| 63 | Kelvin Vasquez | 16 | 2015-2021 | |
| 63 | Kyle Wilson# | 16 | 2020-2023 | |
| 63 | Angel Yepez | 16 | 2018-2021 | |
| 72 | D.J. Baxendale | 15 | 2014-2015 | |
| 72 | Parker Bridwell | 15 | 2014-2022 | |
| 72 | Edgar De La Rosa | 15 | 2014-2017 | |
| 72 | Gray Fenter# | 15 | 2017-2023 | |
| 72 | Jeff Ferrell | 15 | 2014-2015 | |
| 72 | Justin Garza | 15 | 2017-2021 | |
| 72 | Nick Hanson# | 15 | 2018-2022 | |
| 72 | Nick Hernandez# | 15 | 2018-2023 | |
| 72 | Jackson Kowar# | 15 | 2020-2021 | |
| 72 | Max Kuhns# | 15 | 2018-2023 | |
| 72 | Leandro Linares# | 15 | 2019-2023 | |
| 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 | Armando Rivero | 15 | 2015-2017 | |
| 72 | Joe Ross# | 15 | 2014-2015 | |
| 72 | Austin Sodders | 15 | 2019-2021 | |
| 72 | Eric Wooten | 15 | 2017-2017 | |
| 92 | Nathan Alexander | 14 | 2020-2021 | |
| 92 | Xavier Altamirano | 14 | 2019-2022 | |
| 92 | Jeremy Bleich | 14 | 2013-2018 | |
| 92 | Henry Centeno | 14 | 2017-2021 | |
| 92 | Ralph Garza# | 14 | 2018-2023 | |
| 92 | Myles Jaye | 14 | 2013-2015 | |
| 92 | Trey Jeans# | 14 | 2021-2023 | |
| 92 | Brandon G. Koch# | 14 | 2019-2021 | |
| 92 | Brendon Little# | 14 | 2018-2022 |
