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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 | |
| 4 | Josh Rogers# | 3 | 2016-2026 | |
| 9 | Domingo Acevedo# | 2 | 2016-2018 | |
| 9 | Sam Bachman# | 2 | 2022-2024 | |
| 9 | Cam Bedrosian | 2 | 2020-2020 | |
| 9 | Vicente Campos | 2 | 2013-2019 | |
| 9 | Jesus R. Castillo | 2 | 2019-2022 | |
| 9 | Cade Denton# | 2 | 2025-2025 | |
| 9 | Will Hibbs | 2 | 2020-2020 | |
| 9 | Chad Kuhl# | 2 | 2023-2026 | |
| 9 | Pablo Lopez# | 2 | 2018-2018 | |
| 9 | Angel Macuare# | 2 | 2022-2025 | |
| 9 | Griffin McLarty# | 2 | 2022-2026 | |
| 9 | Tyler Rogers# | 2 | 2015-2017 | |
| 9 | Drew Rucinski# | 2 | 2026-2026 | |
| 9 | Jose Urena# | 2 | 2013-2019 | |
| 9 | Nick Vespi# | 2 | 2022-2022 | |
| 24 | Timothy Adleman | 1 | 2015-2020 | |
| 24 | Jose Albertos | 1 | 2019-2022 | |
| 24 | Edgar Arredondo# | 1 | 2020-2026 | |
| 24 | Joe Barlow# | 1 | 2019-2022 | |
| 24 | Aaron Barrett | 1 | 2023-2023 | |
| 24 | Blake Bass | 1 | 2016-2022 | |
| 24 | D.J. Baxendale | 1 | 2016-2017 | |
| 24 | Michael Brady | 1 | 2014-2014 | |
| 24 | Matt Brosky# | 1 | 2024-2025 | |
| 24 | David Buchanan# | 1 | 2023-2026 | |
| 24 | Hever Bueno | 1 | 2019-2022 | |
| 24 | Mike Burrows# | 1 | 2023-2023 | |
| 24 | Kelvin Caceres# | 1 | 2024-2025 | |
| 24 | Matt Canterino# | 1 | 2021-2022 | |
| 24 | Gerardo Carrillo# | 1 | 2022-2022 | |
| 24 | Derek Casey# | 1 | 2022-2025 | |
| 24 | Tim Cate# | 1 | 2020-2026 | |
| 24 | Cade Cavalli# | 1 | 2021-2022 | |
| 24 | Trevor Clifton# | 1 | 2018-2019 | |
| 24 | Austin Coley | 1 | 2016-2019 | |
| 24 | Zac Curtis# | 1 | 2017-2024 | |
| 24 | Noah Davis# | 1 | 2023-2026 | |
| 24 | Seth Davis | 1 | 2016-2017 | |
| 24 | Rafael De Paula | 1 | 2016-2016 | |
| 24 | Pat Dean | 1 | 2013-2015 | |
| 24 | Dean Deetz | 1 | 2018-2020 | |
| 24 | Yefri Del Rosario# | 1 | 2021-2025 | |
| 24 | Odrisamer Despaigne# | 1 | 2023-2024 | |
| 24 | Wilber Dotel# | 1 | 2026-2026 | |
| 24 | Carl Edwards Jr.# | 1 | 2013-2016 | |
| 24 | Scott Engler# | 1 | 2018-2022 | |
| 24 | Blayne Enlow# | 1 | 2020-2025 | |
| 24 | Peter Fairbanks# | 1 | 2019-2019 | |
| 24 | Justin Ferrell | 1 | 2018-2019 | |
| 24 | Ryan Forcucci# | 1 | 2025-2026 | |
| 24 | Patrick Francescon | 1 | 2013-2015 | |
| 24 | Deivi Garcia# | 1 | 2022-2026 | |
| 24 | Edgar Gonzalez | 1 | 2020-2020 | |
| 24 | Severino Gonzalez | 1 | 2017-2017 | |
| 24 | Kevin Gowdy# | 1 | 2024-2025 | |
| 24 | Nate Griep | 1 | 2018-2022 | |
| 24 | Mark Hamburger | 1 | 2020-2020 | |
| 24 | Caleb Hamrick | 1 | 2021-2021 | |
| 24 | Nic Hanson | 1 | 2016-2017 | |
| 24 | Conor Harber | 1 | 2016-2021 | |
| 24 | Nick Hernandez# | 1 | 2020-2021 | |
| 24 | Williams Jerez | 1 | 2017-2017 | |
| 24 | Dany Jimenez# | 1 | 2022-2022 | |
| 24 | Eric Jokisch# | 1 | 2024-2025 | |
| 24 | Casey Kelly# | 1 | 2023-2026 | |
| 24 | Branden Kline | 1 | 2014-2016 | |
| 24 | Michael Knorr# | 1 | 2024-2026 | |
| 24 | Ben Kudrna# | 1 | 2022-2024 | |
| 24 | Jacob Lee | 1 | 2014-2016 | |
| 24 | Victor Lizarraga# | 1 | 2026-2026 | |
| 24 | Reid Love | 1 | 2018-2023 | |
| 24 | Luis Lugo# | 1 | 2017-2017 | |
| 24 | Jake Lyons# | 1 | 2020-2025 | |
| 24 | Tommy Mace# | 1 | 2022-2022 | |
| 24 | Jose M. Marte# | 1 | 2023-2025 | |
| 24 | James Marvel | 1 | 2021-2023 | |
| 24 | Pearson McMahan# | 1 | 2023-2025 | |
| 24 | Adalberto Mejia | 1 | 2016-2016 | |
| 24 | Troy Melton# | 1 | 2023-2024 | |
| 24 | Juan Minaya | 1 | 2020-2022 | |
| 24 | Frankie Montas# | 1 | 2026-2026 | |
| 24 | Gabe Mosser# | 1 | 2022-2026 | |
| 24 | Patrick Murphy# | 1 | 2023-2025 | |
| 24 | TJ Nichols# | 1 | 2025-2025 | |
| 24 | Justin Nicolino | 1 | 2014-2014 | |
| 24 | Mike Nikorak | 1 | 2020-2022 | |
| 24 | Dillon Peters# | 1 | 2023-2026 | |
| 24 | Tyler Phillips# | 1 | 2019-2020 | |
| 24 | Riley Pint# | 1 | 2017-2026 | |
| 24 | Luis Ramirez | 1 | 2016-2018 | |
| 24 | Luis Reyes# | 1 | 2020-2025 | |
| 24 | Houston Roth# | 1 | 2024-2025 |
