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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 | Cade Denton# | 2 | 2025-2025 | |
| 8 | Will Hibbs | 2 | 2020-2020 | |
| 8 | Chad Kuhl# | 2 | 2023-2025 | |
| 8 | Pablo Lopez# | 2 | 2018-2018 | |
| 8 | Angel Macuare# | 2 | 2022-2025 | |
| 8 | Griffin McLarty# | 2 | 2022-2025 | |
| 8 | Tyler Rogers# | 2 | 2015-2017 | |
| 8 | Jose Urena# | 2 | 2013-2019 | |
| 8 | Nick Vespi# | 2 | 2022-2022 | |
| 22 | Timothy Adleman | 1 | 2015-2020 | |
| 22 | Jose Albertos# | 1 | 2019-2022 | |
| 22 | Edgar Arredondo# | 1 | 2020-2025 | |
| 22 | Joe Barlow# | 1 | 2019-2022 | |
| 22 | Aaron Barrett | 1 | 2023-2023 | |
| 22 | Blake Bass | 1 | 2016-2022 | |
| 22 | D.J. Baxendale | 1 | 2016-2017 | |
| 22 | Michael Brady | 1 | 2014-2014 | |
| 22 | Matt Brosky# | 1 | 2024-2025 | |
| 22 | David Buchanan# | 1 | 2023-2025 | |
| 22 | Hever Bueno | 1 | 2019-2022 | |
| 22 | Mike Burrows# | 1 | 2023-2023 | |
| 22 | Kelvin Caceres# | 1 | 2024-2025 | |
| 22 | Matt Canterino# | 1 | 2021-2022 | |
| 22 | Gerardo Carrillo# | 1 | 2022-2022 | |
| 22 | Derek Casey# | 1 | 2022-2025 | |
| 22 | Tim Cate# | 1 | 2020-2024 | |
| 22 | Cade Cavalli# | 1 | 2021-2022 | |
| 22 | Trevor Clifton# | 1 | 2018-2019 | |
| 22 | Austin Coley | 1 | 2016-2019 | |
| 22 | Zac Curtis# | 1 | 2017-2024 | |
| 22 | Seth Davis | 1 | 2016-2017 | |
| 22 | Rafael De Paula | 1 | 2016-2016 | |
| 22 | Pat Dean | 1 | 2013-2015 | |
| 22 | Dean Deetz | 1 | 2018-2020 | |
| 22 | Yefri Del Rosario# | 1 | 2021-2025 | |
| 22 | Odrisamer Despaigne# | 1 | 2023-2024 | |
| 22 | Carl Edwards Jr.# | 1 | 2013-2016 | |
| 22 | Scott Engler# | 1 | 2018-2022 | |
| 22 | Blayne Enlow# | 1 | 2020-2025 | |
| 22 | Peter Fairbanks# | 1 | 2019-2019 | |
| 22 | Justin Ferrell | 1 | 2018-2019 | |
| 22 | Patrick Francescon | 1 | 2013-2015 | |
| 22 | Edgar Gonzalez | 1 | 2020-2020 | |
| 22 | Severino Gonzalez | 1 | 2017-2017 | |
| 22 | Kevin Gowdy# | 1 | 2024-2025 | |
| 22 | Nate Griep | 1 | 2018-2022 | |
| 22 | Mark Hamburger | 1 | 2020-2020 | |
| 22 | Caleb Hamrick | 1 | 2021-2021 | |
| 22 | Nic Hanson | 1 | 2016-2017 | |
| 22 | Conor Harber | 1 | 2016-2021 | |
| 22 | Nick Hernandez# | 1 | 2020-2021 | |
| 22 | Williams Jerez | 1 | 2017-2017 | |
| 22 | Dany Jimenez# | 1 | 2022-2022 | |
| 22 | Eric Jokisch# | 1 | 2024-2025 | |
| 22 | Casey Kelly# | 1 | 2023-2025 | |
| 22 | Branden Kline | 1 | 2014-2016 | |
| 22 | Ben Kudrna# | 1 | 2022-2024 | |
| 22 | Jacob Lee | 1 | 2014-2016 | |
| 22 | Reid Love | 1 | 2018-2023 | |
| 22 | Luis Lugo# | 1 | 2017-2017 | |
| 22 | Jake Lyons# | 1 | 2020-2025 | |
| 22 | Tommy Mace# | 1 | 2022-2022 | |
| 22 | Jose M. Marte# | 1 | 2023-2025 | |
| 22 | James Marvel | 1 | 2021-2023 | |
| 22 | Pearson McMahan# | 1 | 2023-2025 | |
| 22 | Adalberto Mejia | 1 | 2016-2016 | |
| 22 | Troy Melton# | 1 | 2023-2024 | |
| 22 | Juan Minaya | 1 | 2020-2022 | |
| 22 | Gabe Mosser# | 1 | 2022-2025 | |
| 22 | Patrick Murphy# | 1 | 2023-2025 | |
| 22 | TJ Nichols# | 1 | 2025-2025 | |
| 22 | Justin Nicolino | 1 | 2014-2014 | |
| 22 | Mike Nikorak | 1 | 2020-2022 | |
| 22 | Dillon Peters# | 1 | 2023-2024 | |
| 22 | Tyler Phillips# | 1 | 2019-2020 | |
| 22 | Luis Ramirez | 1 | 2016-2018 | |
| 22 | Luis Reyes# | 1 | 2020-2025 | |
| 22 | Josh Rogers# | 1 | 2016-2025 | |
| 22 | Houston Roth# | 1 | 2024-2025 | |
| 22 | Gregory Santos# | 1 | 2021-2023 | |
| 22 | Nicholas Sawyer | 1 | 2016-2016 | |
| 22 | J.P. Sears# | 1 | 2019-2021 | |
| 22 | Charlie Shirek | 1 | 2016-2016 | |
| 22 | D.J. Snelten | 1 | 2017-2019 | |
| 22 | Giovanni Soto | 1 | 2013-2014 | |
| 22 | Jackson Stephens# | 1 | 2015-2015 | |
| 22 | Scotty Sunitsch | 1 | 2021-2021 | |
| 22 | Ryan Thompson# | 1 | 2016-2019 |
