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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Joey DeNato | 4 | 2018-2018 | |
| 2 | Jose De Paula | 3 | 2013-2014 | |
| 2 | Ivan Pineyro | 3 | 2014-2019 | |
| 2 | Brady Rodgers | 3 | 2015-2016 | |
| 5 | John Anderson | 2 | 2013-2015 | |
| 5 | Jordan Balazovic# | 2 | 2023-2023 | |
| 5 | Andrew Barbosa | 2 | 2014-2017 | |
| 5 | Calvin Coker# | 2 | 2020-2025 | |
| 5 | Jason Foley# | 2 | 2018-2021 | |
| 5 | Ian Gibaut# | 2 | 2018-2022 | |
| 5 | Austin Glorius | 2 | 2016-2021 | |
| 5 | Brennan Hanifee# | 2 | 2019-2024 | |
| 5 | Tink Hence# | 2 | 2023-2025 | |
| 5 | Spencer Jones | 2 | 2018-2020 | |
| 5 | Kyle Lloyd | 2 | 2017-2019 | |
| 5 | Hector Lujan# | 2 | 2016-2025 | |
| 5 | Evan Manarino | 2 | 2019-2021 | |
| 5 | Matt Milburn | 2 | 2019-2022 | |
| 5 | Aaron Northcraft | 2 | 2021-2021 | |
| 5 | Garrett Nuss | 2 | 2014-2017 | |
| 5 | Ryan Robowski | 2 | 2013-2015 | |
| 5 | A.J. Schugel | 2 | 2019-2021 | |
| 5 | Kelvin Vasquez | 2 | 2015-2021 | |
| 5 | Tyler Ybarra | 2 | 2014-2014 | |
| 5 | Luis Ysla | 2 | 2016-2020 | |
| 5 | Noah Zavolas# | 2 | 2023-2025 | |
| 27 | Brandon Allen | 1 | 2014-2017 | |
| 27 | Victor Araujo | 1 | 2020-2021 | |
| 27 | Trent Baker# | 1 | 2022-2024 | |
| 27 | Ryan Bean | 1 | 2013-2017 | |
| 27 | Will Bednar# | 1 | 2023-2025 | |
| 27 | Marc Berube | 1 | 2017-2017 | |
| 27 | Blake Bivens | 1 | 2016-2016 | |
| 27 | Seth Blair | 1 | 2020-2021 | |
| 27 | Cam Booser# | 1 | 2024-2024 | |
| 27 | Matthew Boyd# | 1 | 2014-2016 | |
| 27 | Zach Brzykcy# | 1 | 2023-2023 | |
| 27 | Dan Camarena# | 1 | 2021-2024 | |
| 27 | Matt Carasiti# | 1 | 2019-2019 | |
| 27 | Henry Centeno | 1 | 2017-2017 | |
| 27 | Jaye Chapman | 1 | 2016-2016 | |
| 27 | Cole Coshow | 1 | 2017-2020 | |
| 27 | Matt Davenport | 1 | 2016-2017 | |
| 27 | Nick Davila# | 1 | 2024-2025 | |
| 27 | Miguel Diaz# | 1 | 2017-2018 | |
| 27 | Brian Dupra | 1 | 2013-2013 | |
| 27 | Jon Edwards | 1 | 2015-2020 | |
| 27 | Scott Elbert | 1 | 2017-2017 | |
| 27 | Trevor Frank | 1 | 2017-2021 | |
| 27 | Kyle Friedrichs | 1 | 2020-2020 | |
| 27 | Brandyn Garcia# | 1 | 2023-2025 | |
| 27 | Rico Garcia# | 1 | 2018-2024 | |
| 27 | Trent Garrison | 1 | 2014-2016 | |
| 27 | Justin Garza# | 1 | 2021-2024 | |
| 27 | Joe Gatto | 1 | 2019-2022 | |
| 27 | J.T. Ginn# | 1 | 2023-2024 | |
| 27 | Brandon Gold | 1 | 2018-2022 | |
| 27 | Nelson Gonzalez | 1 | 2013-2023 | |
| 27 | Regi Grace# | 1 | 2024-2024 | |
| 27 | Foster Griffin# | 1 | 2021-2022 | |
| 27 | David Hale | 1 | 2020-2020 | |
| 27 | Josh Hendrickson# | 1 | 2021-2025 | |
| 27 | Edgardo Henriquez# | 1 | 2023-2025 | |
| 27 | Juan Hillman# | 1 | 2020-2025 | |
| 27 | Chad Hockin | 1 | 2018-2021 | |
| 27 | T.J. House | 1 | 2013-2014 | |
| 27 | Jake Irvin# | 1 | 2020-2022 | |
| 27 | Williams Jerez | 1 | 2014-2021 | |
| 27 | Joe Jimenez# | 1 | 2017-2021 | |
| 27 | Boby Johnson# | 1 | 2022-2024 | |
| 27 | Zachary Jones | 1 | 2018-2019 | |
| 27 | Joseph King# | 1 | 2025-2025 | |
| 27 | Nick Lackney# | 1 | 2024-2025 | |
| 27 | Jared Lakind | 1 | 2014-2017 | |
| 27 | Holden Laws# | 1 | 2024-2025 | |
| 27 | Jake Lemoine | 1 | 2016-2023 | |
| 27 | Luis Madero# | 1 | 2020-2025 | |
| 27 | David Martinez | 1 | 2013-2016 | |
| 27 | Mason McCullough | 1 | 2019-2021 | |
| 27 | Nick Mears# | 1 | 2021-2024 | |
| 27 | Cristian Mena# | 1 | 2023-2024 | |
| 27 | Bryan Mitchell | 1 | 2021-2023 | |
| 27 | McKinley Moore# | 1 | 2023-2024 | |
| 27 | Benton Moss | 1 | 2016-2020 | |
| 27 | Aaron Munson# | 1 | 2025-2025 | |
| 27 | Michael Murray | 1 | 2017-2021 | |
| 27 | Joe Musgrove# | 1 | 2016-2016 | |
| 27 | Packy Naughton# | 1 | 2020-2022 | |
| 27 | Jake Newberry | 1 | 2018-2022 | |
| 27 | Sean Newcomb# | 1 | 2017-2025 | |
| 27 | Tyler Olson | 1 | 2015-2017 | |
| 27 | Josh Osich | 1 | 2013-2021 | |
| 27 | Andy Otero | 1 | 2021-2021 | |
| 27 | Kai Peterson# | 1 | 2025-2025 | |
| 27 | Andrew Politi# | 1 | 2020-2024 | |
| 27 | Benino Pruneda | 1 | 2013-2016 | |
| 27 | Jake Reed# | 1 | 2019-2025 | |
| 27 | Francisco Rios# | 1 | 2019-2022 | |
| 27 | Tom Robson | 1 | 2015-2022 | |
| 27 | Angel Rondon# | 1 | 2021-2022 |
