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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Jay Jackson# | 5 | 2013-2021 | |
| 2 | Jimmy Gillheeney | 4 | 2013-2015 | |
| 2 | Tyler Glasnow# | 4 | 2014-2015 | |
| 4 | Eric Hacker | 3 | 2017-2022 | |
| 4 | Christopher Kirsch | 3 | 2016-2017 | |
| 4 | Matt Purke | 3 | 2014-2017 | |
| 4 | Reid Redman | 3 | 2013-2019 | |
| 8 | Domingo Acevedo# | 2 | 2016-2018 | |
| 8 | Sam Bachman# | 2 | 2022-2024 | |
| 8 | Cam Bedrosian | 2 | 2020-2020 | |
| 8 | Vicente Campos | 2 | 2013-2019 | |
| 8 | Jesus R. Castillo | 2 | 2019-2022 | |
| 8 | Will Hibbs | 2 | 2020-2020 | |
| 8 | Chad Kuhl# | 2 | 2023-2025 | |
| 8 | Pablo Lopez# | 2 | 2018-2018 | |
| 8 | Angel Macuare# | 2 | 2022-2024 | |
| 8 | Tyler Rogers# | 2 | 2015-2017 | |
| 8 | Jose Urena# | 2 | 2013-2019 | |
| 8 | Nick Vespi# | 2 | 2022-2022 | |
| 20 | Timothy Adleman | 1 | 2015-2020 | |
| 20 | Jose Albertos# | 1 | 2019-2022 | |
| 20 | Joe Barlow# | 1 | 2019-2022 | |
| 20 | Aaron Barrett | 1 | 2023-2023 | |
| 20 | Blake Bass | 1 | 2016-2022 | |
| 20 | D.J. Baxendale | 1 | 2016-2017 | |
| 20 | Michael Brady | 1 | 2014-2014 | |
| 20 | Matt Brosky# | 1 | 2024-2024 | |
| 20 | David Buchanan# | 1 | 2023-2025 | |
| 20 | Hever Bueno | 1 | 2019-2022 | |
| 20 | Michael Burrows# | 1 | 2023-2023 | |
| 20 | Kelvin Caceres# | 1 | 2024-2024 | |
| 20 | Matt Canterino# | 1 | 2021-2022 | |
| 20 | Gerardo Carrillo# | 1 | 2022-2022 | |
| 20 | Derek Casey# | 1 | 2022-2025 | |
| 20 | Tim Cate# | 1 | 2020-2024 | |
| 20 | Cade Cavalli# | 1 | 2021-2022 | |
| 20 | Trevor Clifton# | 1 | 2018-2019 | |
| 20 | Austin Coley | 1 | 2016-2019 | |
| 20 | Zac Curtis# | 1 | 2017-2024 | |
| 20 | Seth Davis | 1 | 2016-2017 | |
| 20 | Rafael De Paula | 1 | 2016-2016 | |
| 20 | Pat Dean | 1 | 2013-2015 | |
| 20 | Dean Deetz | 1 | 2018-2020 | |
| 20 | Yefri Del Rosario# | 1 | 2021-2025 | |
| 20 | Odrisamer Despaigne# | 1 | 2023-2024 | |
| 20 | Carl Edwards Jr.# | 1 | 2013-2016 | |
| 20 | Scott Engler# | 1 | 2018-2022 | |
| 20 | Blayne Enlow# | 1 | 2020-2024 | |
| 20 | Peter Fairbanks# | 1 | 2019-2019 | |
| 20 | Justin Ferrell | 1 | 2018-2019 | |
| 20 | Patrick Francescon | 1 | 2013-2015 | |
| 20 | Edgar Gonzalez | 1 | 2020-2020 | |
| 20 | Severino Gonzalez | 1 | 2017-2017 | |
| 20 | Kevin Gowdy# | 1 | 2024-2025 | |
| 20 | Nate Griep | 1 | 2018-2022 | |
| 20 | Mark Hamburger | 1 | 2020-2020 | |
| 20 | Caleb Hamrick | 1 | 2021-2021 | |
| 20 | Nic Hanson | 1 | 2016-2017 | |
| 20 | Conor Harber | 1 | 2016-2021 | |
| 20 | Nick Hernandez# | 1 | 2020-2021 | |
| 20 | Williams Jerez | 1 | 2017-2017 | |
| 20 | Dany Jimenez# | 1 | 2022-2022 | |
| 20 | Eric Jokisch# | 1 | 2024-2025 | |
| 20 | Casey Kelly# | 1 | 2023-2025 | |
| 20 | Branden Kline | 1 | 2014-2016 | |
| 20 | Ben Kudrna# | 1 | 2022-2024 | |
| 20 | Jacob Lee | 1 | 2014-2016 | |
| 20 | Reid Love | 1 | 2018-2023 | |
| 20 | Luis Lugo# | 1 | 2017-2017 | |
| 20 | Tommy Mace# | 1 | 2022-2022 | |
| 20 | James Marvel | 1 | 2021-2023 | |
| 20 | Pearson McMahan# | 1 | 2023-2025 | |
| 20 | Adalberto Mejia | 1 | 2016-2016 | |
| 20 | Troy Melton# | 1 | 2023-2024 | |
| 20 | Juan Minaya | 1 | 2020-2022 | |
| 20 | Patrick Murphy# | 1 | 2023-2025 | |
| 20 | Justin Nicolino | 1 | 2014-2014 | |
| 20 | Mike Nikorak | 1 | 2020-2022 | |
| 20 | Dillon Peters# | 1 | 2023-2024 | |
| 20 | Tyler Phillips# | 1 | 2019-2020 | |
| 20 | Luis Ramirez | 1 | 2016-2018 | |
| 20 | Luis Reyes# | 1 | 2020-2024 | |
| 20 | Gregory Santos# | 1 | 2021-2023 | |
| 20 | Nicholas Sawyer | 1 | 2016-2016 | |
| 20 | J.P. Sears# | 1 | 2019-2021 | |
| 20 | Charlie Shirek | 1 | 2016-2016 | |
| 20 | D.J. Snelten | 1 | 2017-2019 | |
| 20 | Giovanni Soto | 1 | 2013-2014 | |
| 20 | Jackson Stephens# | 1 | 2015-2015 | |
| 20 | Scotty Sunitsch | 1 | 2021-2021 | |
| 20 | Ryan Thompson# | 1 | 2016-2019 | |
| 20 | Blade Tidwell# | 1 | 2023-2024 | |
| 20 | Julio Urias# | 1 | 2015-2016 | |
| 20 | Mike Vasil# | 1 | 2023-2024 | |
| 20 | Blake Whitney# | 1 | 2022-2023 | |
| 20 | Angel Zerpa# | 1 | 2023-2023 | |
| 97 | Andury Acevedo | 0 | 2015-2017 | |
| 97 | Adam Achter | 0 | 2013-2017 | |
| 97 | Dane Acker# | 0 | 2022-2023 | |
| 97 | Brady Aiken | 0 | 2018-2019 |
