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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Erick Leal | 38 | 2018-2021 | |
| 2 | Jeff Ames | 36 | 2014-2017 | |
| 3 | Tanner Peters | 34 | 2013-2016 | |
| 4 | Mason Radeke | 33 | 2014-2018 | |
| 5 | Parker Markel# | 32 | 2013-2016 | |
| 6 | Jordan Pries | 30 | 2013-2016 | |
| 6 | Jake Stinnett | 30 | 2017-2021 | |
| 8 | Denyi Reyes# | 29 | 2020-2022 | |
| 9 | Jose Taveras | 28 | 2019-2023 | |
| 10 | Ian Clarkin# | 27 | 2015-2023 | |
| 10 | Darin Gillies# | 27 | 2016-2023 | |
| 10 | A.J. Ladwig# | 27 | 2017-2022 | |
| 13 | Chris Mazza# | 25 | 2015-2019 | |
| 13 | Gus Varland# | 25 | 2020-2022 | |
| 15 | Matt Brazis | 24 | 2013-2016 | |
| 15 | Manaure Martinez | 24 | 2014-2016 | |
| 17 | Parker Bridwell | 23 | 2014-2022 | |
| 17 | Ian Gardeck | 23 | 2014-2019 | |
| 17 | Ryan Kellogg | 23 | 2017-2021 | |
| 17 | Brendon Little# | 23 | 2018-2022 | |
| 21 | Chase Huchingson | 22 | 2013-2016 | |
| 22 | Josh Winder# | 21 | 2020-2021 | |
| 23 | Jonathan Dziedzic | 20 | 2014-2015 | |
| 23 | Silfredo Garcia | 20 | 2014-2016 | |
| 23 | Max Lazar# | 20 | 2018-2022 | |
| 26 | Jayson Aquino | 19 | 2014-2016 | |
| 26 | Andy Beltre | 19 | 2014-2016 | |
| 26 | Gustavo Gomez | 19 | 2014-2016 | |
| 26 | Dallas Litscher# | 19 | 2019-2022 | |
| 26 | Dalton Moats# | 19 | 2019-2023 | |
| 31 | Alex Black | 18 | 2014-2017 | |
| 31 | Andrew Lee | 18 | 2016-2020 | |
| 31 | Ronald Pena | 18 | 2016-2020 | |
| 31 | Chris Rowley | 18 | 2017-2021 | |
| 31 | Brian Shaffer# | 18 | 2019-2021 | |
| 31 | Jesus Tinoco# | 18 | 2019-2023 | |
| 31 | Stephen Woods Jr.# | 18 | 2020-2023 | |
| 38 | Tommy Doyle# | 17 | 2018-2023 | |
| 38 | Ismael Guillon | 17 | 2017-2019 | |
| 38 | Kyle Hunter | 17 | 2013-2017 | |
| 38 | Scott McGough# | 17 | 2013-2015 | |
| 38 | Sean Poppen# | 17 | 2018-2023 | |
| 38 | Dae-Eun Rhee | 17 | 2013-2014 | |
| 44 | Jon Harris# | 16 | 2018-2020 | |
| 44 | Robbie Hitt# | 16 | 2018-2023 | |
| 44 | Eduardo Rodriguez# | 16 | 2014-2015 | |
| 44 | Chad Thompson | 16 | 2014-2016 | |
| 48 | Solomon Bates# | 15 | 2020-2022 | |
| 48 | Jesse Biddle# | 15 | 2013-2013 | |
| 48 | Jordan Johnson | 15 | 2017-2020 | |
| 48 | Brian Miller# | 15 | 2017-2019 | |
| 48 | Jose Mujica# | 15 | 2019-2023 | |
| 48 | Ofelky Peralta# | 15 | 2016-2023 | |
| 48 | John Rooney# | 15 | 2020-2022 | |
| 48 | Mike Ruff# | 15 | 2020-2023 | |
| 48 | Timothy Shibuya | 15 | 2014-2018 | |
| 48 | Will Stewart# | 15 | 2016-2023 | |
| 58 | Kyle Bartsch | 14 | 2014-2017 | |
| 58 | Connor Grey# | 14 | 2018-2021 | |
| 58 | Casey Harman | 14 | 2013-2018 | |
| 58 | David Lebron# | 14 | 2019-2021 | |
| 58 | Anthony Misiewicz# | 14 | 2019-2020 | |
| 58 | Jorge Ortega | 14 | 2017-2019 | |
| 58 | Robinson Ortiz# | 14 | 2020-2023 | |
| 58 | Domingo Robles# | 14 | 2019-2020 | |
| 58 | Chris Rodriguez# | 14 | 2019-2020 | |
| 58 | Tony Santillan# | 14 | 2018-2020 | |
| 58 | Adam Scott# | 14 | 2020-2021 | |
| 58 | Trent Szkutnik | 14 | 2016-2020 | |
| 58 | Benjamin Wells | 14 | 2016-2017 | |
| 71 | A.J. Alexy# | 13 | 2020-2023 | |
| 71 | Manny Banuelos# | 13 | 2013-2013 | |
| 71 | Jacob Dahlstrand | 13 | 2015-2016 | |
| 71 | Luis Diaz | 13 | 2014-2014 | |
| 71 | Bryan Dobzanski# | 13 | 2020-2022 | |
| 71 | Tyler Dyson# | 13 | 2022-2023 | |
| 71 | Raul Fernandez | 13 | 2014-2017 | |
| 71 | Michael Fulmer# | 13 | 2013-2015 | |
| 71 | Edgar Garcia# | 13 | 2017-2023 | |
| 71 | Mack Lemieux# | 13 | 2017-2023 | |
| 71 | Michael Matuella | 13 | 2016-2022 | |
| 71 | Erling Moreno# | 13 | 2019-2021 | |
| 71 | Kyle Nelson# | 13 | 2019-2022 | |
| 71 | Braeden Ogle# | 13 | 2019-2023 | |
| 71 | Zach Schellenger | 13 | 2019-2022 | |
| 71 | Tyler Watson# | 13 | 2017-2020 | |
| 87 | Robert Benincasa | 12 | 2014-2016 | |
| 87 | Mike Broadway | 12 | 2013-2015 | |
| 87 | Chris Gau# | 12 | 2020-2023 | |
| 87 | Cameron Hobson | 12 | 2014-2015 | |
| 87 | Corey Littrell | 12 | 2021-2021 | |
| 87 | Kevin McAvoy | 12 | 2018-2019 | |
| 87 | Patrick McGuff | 12 | 2018-2021 | |
| 87 | Jon Olsen# | 12 | 2022-2023 | |
| 87 | Peyton Remy# | 12 | 2020-2023 | |
| 87 | Jackson Stephens# | 12 | 2020-2021 | |
| 87 | Alex Valverde# | 12 | 2018-2023 | |
| 87 | Blair Walters | 12 | 2013-2017 | |
| 87 | Asher Wojciechowski# | 12 | 2021-2021 | |
| 100 | Austin Cox# | 11 | 2019-2021 |
