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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Jake Stinnett | 4 | 2017-2021 | |
| 2 | Ryley Gilliam | 3 | 2020-2023 | |
| 2 | Parker Markel | 3 | 2013-2016 | |
| 4 | Braxton Ashcraft# | 2 | 2022-2023 | |
| 4 | Taj Bradley# | 2 | 2019-2021 | |
| 4 | Matt Brazis | 2 | 2013-2016 | |
| 4 | Parker Bridwell | 2 | 2014-2022 | |
| 4 | Dylan Cease# | 2 | 2016-2017 | |
| 4 | Andrew Church | 2 | 2015-2018 | |
| 4 | Marcos Diplan | 2 | 2021-2021 | |
| 4 | Bryan Evans | 2 | 2015-2016 | |
| 4 | Raul Fernandez | 2 | 2014-2017 | |
| 4 | Nick Fraze# | 2 | 2022-2025 | |
| 4 | Grayson Garvin | 2 | 2013-2014 | |
| 4 | Kevin McAvoy | 2 | 2018-2019 | |
| 4 | Nick Neidert# | 2 | 2017-2018 | |
| 4 | Liam Norris# | 2 | 2024-2025 | |
| 4 | Jack Perkins# | 2 | 2023-2025 | |
| 4 | Tanner Peters | 2 | 2013-2016 | |
| 4 | Chris Rodriguez# | 2 | 2019-2025 | |
| 4 | Blake Schwartz | 2 | 2014-2016 | |
| 4 | Billy Strode | 2 | 2016-2017 | |
| 4 | Ryan Walker# | 2 | 2022-2023 | |
| 4 | Jimmy Yacabonis | 2 | 2014-2015 | |
| 25 | Tejay Antone# | 1 | 2025-2025 | |
| 25 | Clark Beeker | 1 | 2017-2019 | |
| 25 | Valente Bellozo# | 1 | 2023-2024 | |
| 25 | Greg Belton | 1 | 2018-2018 | |
| 25 | Denny Bentley# | 1 | 2023-2025 | |
| 25 | Jesse Biddle | 1 | 2013-2013 | |
| 25 | Nick Bitsko# | 1 | 2025-2025 | |
| 25 | Ryan Burr# | 1 | 2018-2018 | |
| 25 | Isaiah Campbell# | 1 | 2021-2023 | |
| 25 | Eiberson Castellano# | 1 | 2025-2025 | |
| 25 | Austin Cates# | 1 | 2025-2025 | |
| 25 | Miguel Celestino | 1 | 2013-2014 | |
| 25 | Austin Cox# | 1 | 2019-2021 | |
| 25 | Jacob Dahlstrand | 1 | 2015-2016 | |
| 25 | Colton Davis | 1 | 2018-2019 | |
| 25 | Nick Dean# | 1 | 2025-2025 | |
| 25 | James Dykstra | 1 | 2020-2023 | |
| 25 | William Fleming# | 1 | 2024-2025 | |
| 25 | Justin Garza# | 1 | 2016-2019 | |
| 25 | Gary Gill Hill# | 1 | 2024-2025 | |
| 25 | Gustavo Gomez | 1 | 2014-2016 | |
| 25 | Ismael Guillon | 1 | 2017-2019 | |
| 25 | Troy Guthrie# | 1 | 2025-2025 | |
| 25 | DJ Herz# | 1 | 2022-2023 | |
| 25 | Nolan Hoffman# | 1 | 2020-2025 | |
| 25 | Chase Huchingson | 1 | 2013-2016 | |
| 25 | Kyle Hunter | 1 | 2013-2017 | |
| 25 | Eric Jokisch# | 1 | 2013-2014 | |
| 25 | Ryan Kellogg | 1 | 2017-2021 | |
| 25 | Hunter Kiel | 1 | 2019-2021 | |
| 25 | Adam Kloffenstein# | 1 | 2025-2025 | |
| 25 | Max Lazar# | 1 | 2018-2022 | |
| 25 | Erick Leal# | 1 | 2018-2021 | |
| 25 | Jack Leftwich# | 1 | 2023-2024 | |
| 25 | Corey Littrell | 1 | 2021-2021 | |
| 25 | Ryan Lobus# | 1 | 2025-2025 | |
| 25 | Manaure Martinez | 1 | 2014-2016 | |
| 25 | Bryan Mata# | 1 | 2019-2020 | |
| 25 | Brody McCullough# | 1 | 2024-2024 | |
| 25 | Dan McGrath | 1 | 2015-2016 | |
| 25 | Brian Miller | 1 | 2017-2019 | |
| 25 | Anthony Misiewicz# | 1 | 2019-2020 | |
| 25 | Erling Moreno | 1 | 2019-2021 | |
| 25 | Tobias Myers# | 1 | 2019-2020 | |
| 25 | Zach Neff# | 1 | 2020-2023 | |
| 25 | Kyle Nelson# | 1 | 2019-2022 | |
| 25 | Jackson Nezuh# | 1 | 2025-2025 | |
| 25 | Peyton Olejnik# | 1 | 2025-2025 | |
| 25 | Jon Olsen# | 1 | 2022-2025 | |
| 25 | Henry Owens | 1 | 2018-2018 | |
| 25 | Eric Pardinho# | 1 | 2022-2025 | |
| 25 | John Parke | 1 | 2019-2019 | |
| 25 | Josh Pennington | 1 | 2017-2018 | |
| 25 | Tyler Phillips# | 1 | 2023-2025 | |
| 25 | Jordan Pries | 1 | 2013-2016 | |
| 25 | Yefry Ramirez | 1 | 2017-2018 | |
| 25 | Jorge Rodriguez | 1 | 2016-2017 | |
| 25 | Simon Rosenblum-Larson | 1 | 2019-2022 | |
| 25 | Mike Ruff# | 1 | 2020-2024 | |
| 25 | Brian Shaffer | 1 | 2019-2021 | |
| 25 | Jordan Shipers | 1 | 2013-2014 | |
| 25 | Avery Short# | 1 | 2025-2025 | |
| 25 | Hunter Smith | 1 | 2018-2019 | |
| 25 | Jackson Stephens# | 1 | 2020-2021 | |
| 25 | Mitchell Stumpo# | 1 | 2023-2025 | |
| 25 | Cecil Tanner | 1 | 2014-2016 | |
| 25 | Robert Tasin | 1 | 2016-2017 | |
| 25 | Jose Taveras | 1 | 2019-2023 | |
| 25 | Jackson Tetreault# | 1 | 2020-2022 | |
| 25 | Connor Thomas# | 1 | 2020-2022 | |
| 25 | Jesus Tinoco# | 1 | 2019-2023 | |
| 25 | Noe Toribio# | 1 | 2022-2025 | |
| 25 | Jacob Wallace# | 1 | 2020-2025 | |
| 25 | Connor Walsh | 1 | 2018-2020 | |
| 25 | Spenser Watkins# | 1 | 2020-2022 | |
| 25 | Bradley Watson | 1 | 2013-2013 |
