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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Noah Davis# | 3 | 2020-2022 | |
| 1 | Caleb Frare | 3 | 2013-2015 | |
| 1 | Daniel Mengden# | 3 | 2015-2016 | |
| 1 | Ricky Vanasco# | 3 | 2018-2020 | |
| 5 | Garrett Burhenn# | 2 | 2022-2024 | |
| 5 | Trey Dombroski# | 2 | 2024-2025 | |
| 5 | Justin Ferrell | 2 | 2015-2017 | |
| 5 | Edgar Gonzalez | 2 | 2022-2022 | |
| 5 | Anthony Hoopii-Tuionetoa# | 2 | 2021-2024 | |
| 5 | Hayden Hurst | 2 | 2013-2016 | |
| 5 | Tanner Jacobson# | 2 | 2023-2025 | |
| 5 | Seth Johnson# | 2 | 2020-2021 | |
| 5 | Connor Kaden | 2 | 2015-2017 | |
| 5 | Zak Kent# | 2 | 2021-2021 | |
| 5 | John King# | 2 | 2019-2020 | |
| 5 | Dusten Knight | 2 | 2021-2021 | |
| 5 | Austin Krob# | 2 | 2024-2024 | |
| 5 | Gunner Mayer# | 2 | 2020-2024 | |
| 5 | Albert Minnis | 2 | 2014-2016 | |
| 5 | Jaylen Nowlin# | 2 | 2022-2023 | |
| 5 | John Parke | 2 | 2018-2018 | |
| 5 | RJ Petit# | 2 | 2022-2023 | |
| 5 | Julio Pinto | 2 | 2020-2023 | |
| 5 | Storm Rynard | 2 | 2015-2019 | |
| 5 | Jose Taveras | 2 | 2018-2023 | |
| 5 | Nick Yoder | 2 | 2020-2021 | |
| 27 | Travis Adams# | 1 | 2022-2024 | |
| 27 | Jeff Antigua | 1 | 2013-2013 | |
| 27 | Corey Avant# | 1 | 2024-2025 | |
| 27 | Bryan Baker# | 1 | 2017-2021 | |
| 27 | Brian Bayliss | 1 | 2017-2017 | |
| 27 | Nathan Blasick# | 1 | 2025-2025 | |
| 27 | Brandon Bonilla | 1 | 2018-2018 | |
| 27 | Yimmi Brasoban | 1 | 2014-2014 | |
| 27 | Ben Brewster | 1 | 2015-2017 | |
| 27 | Bryan Brickhouse | 1 | 2021-2021 | |
| 27 | Ryan Brown# | 1 | 2024-2025 | |
| 27 | Tyler Brunnemann | 1 | 2016-2017 | |
| 27 | Ethan Carnes | 1 | 2014-2017 | |
| 27 | Damion Carroll | 1 | 2015-2016 | |
| 27 | Bubba Chandler# | 1 | 2022-2024 | |
| 27 | Brandon Clarke# | 1 | 2025-2025 | |
| 27 | Connor Coward | 1 | 2019-2019 | |
| 27 | Dean Deetz | 1 | 2015-2017 | |
| 27 | Randall Fant | 1 | 2017-2017 | |
| 27 | Thomas Farr# | 1 | 2024-2024 | |
| 27 | Julio Felix | 1 | 2013-2019 | |
| 27 | Jefferson Figueroa# | 1 | 2021-2024 | |
| 27 | J.C. Flowers# | 1 | 2025-2025 | |
| 27 | Scott Frazier | 1 | 2014-2017 | |
| 27 | Drake George# | 1 | 2025-2025 | |
| 27 | Spencer Giesting# | 1 | 2023-2024 | |
| 27 | Nick Green | 1 | 2015-2017 | |
| 27 | Justin Haley | 1 | 2013-2014 | |
| 27 | Josh Hansell# | 1 | 2024-2025 | |
| 27 | Charles Harrison# | 1 | 2024-2025 | |
| 27 | Jacob Heatherly# | 1 | 2021-2021 | |
| 27 | Ronald Herrera# | 1 | 2014-2014 | |
| 27 | Chad Hockin | 1 | 2017-2017 | |
| 27 | Cristian Javier# | 1 | 2018-2018 | |
| 27 | Branden Kelliher | 1 | 2015-2018 | |
| 27 | Andrew Leenhouts | 1 | 2013-2013 | |
| 27 | Eli Lingos | 1 | 2019-2024 | |
| 27 | Nick Lockhart# | 1 | 2021-2025 | |
| 27 | Logan Longwith | 1 | 2016-2018 | |
| 27 | Damien Magnifico | 1 | 2014-2015 | |
| 27 | Joey Marciano | 1 | 2019-2021 | |
| 27 | Brandon McNitt | 1 | 2015-2015 | |
| 27 | Tim Melville | 1 | 2017-2017 | |
| 27 | Kenny Mendoza | 1 | 2018-2019 | |
| 27 | Abel Mercedes# | 1 | 2024-2025 | |
| 27 | Jake Mielock | 1 | 2019-2019 | |
| 27 | Joe Mockbee | 1 | 2018-2018 | |
| 27 | Mike Morin | 1 | 2013-2014 | |
| 27 | Gabe Mosser# | 1 | 2020-2024 | |
| 27 | Aaron Nola# | 1 | 2015-2015 | |
| 27 | Braulio Ortiz | 1 | 2019-2019 | |
| 27 | Andrew Painter# | 1 | 2022-2022 | |
| 27 | Inohan Paniagua# | 1 | 2024-2025 | |
| 27 | Geordy Parra | 1 | 2015-2017 | |
| 27 | Brayan Perez# | 1 | 2022-2022 | |
| 27 | Brandon Peterson | 1 | 2014-2017 | |
| 27 | Peyton Plumlee# | 1 | 2020-2022 | |
| 27 | Cole Ragans# | 1 | 2018-2018 | |
| 27 | Manny Ramirez# | 1 | 2023-2025 | |
| 27 | Yefry Ramirez | 1 | 2016-2016 | |
| 27 | Yacksel Rios# | 1 | 2013-2015 | |
| 27 | Adrian Rodriguez# | 1 | 2021-2025 | |
| 27 | Alberto Rodriguez | 1 | 2017-2017 | |
| 27 | Joe Ross# | 1 | 2013-2013 | |
| 27 | Ben Rowen | 1 | 2022-2023 | |
| 27 | Brian Shaffer | 1 | 2018-2018 | |
| 27 | Ryan Sherriff | 1 | 2013-2016 | |
| 27 | Cody Stashak# | 1 | 2016-2025 | |
| 27 | Jordan Stephens | 1 | 2017-2017 | |
| 27 | Daniel Stumpf | 1 | 2013-2013 | |
| 27 | Wander Suero# | 1 | 2016-2016 | |
| 27 | Erik Tolman# | 1 | 2022-2024 | |
| 27 | Jose Torres | 1 | 2015-2016 | |
| 27 | Connor Walsh | 1 | 2015-2016 |
