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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Alec Kisena | 4 | 2022-2024 | |
| 1 | Zach McCambley# | 4 | 2022-2024 | |
| 1 | Jason Stoffel | 4 | 2013-2017 | |
| 1 | Danny Young# | 4 | 2018-2024 | |
| 5 | Christian Binford | 3 | 2015-2016 | |
| 5 | Greg Nappo | 3 | 2016-2018 | |
| 5 | Martin Perez# | 3 | 2013-2019 | |
| 5 | Scott Williams | 3 | 2018-2021 | |
| 9 | Spencer Adams | 2 | 2017-2019 | |
| 9 | Tyler Chatwood | 2 | 2013-2013 | |
| 9 | Brody Colvin | 2 | 2013-2016 | |
| 9 | Isaiah Coupet# | 2 | 2023-2026 | |
| 9 | Matt Gage# | 2 | 2017-2026 | |
| 9 | Kyle Hart# | 2 | 2019-2023 | |
| 9 | Taylor Hearn# | 2 | 2020-2021 | |
| 9 | Alek Jacob# | 2 | 2023-2026 | |
| 9 | Eric Jokisch# | 2 | 2014-2018 | |
| 9 | Connor Loeprich# | 2 | 2023-2024 | |
| 9 | Zachary Lovvorn | 2 | 2019-2021 | |
| 9 | Julian Merryweather# | 2 | 2017-2020 | |
| 9 | Franklin Morales | 2 | 2014-2015 | |
| 9 | Adam Morgan | 2 | 2013-2023 | |
| 9 | Zach Petrick | 2 | 2014-2016 | |
| 9 | Alan Rangel# | 2 | 2022-2025 | |
| 9 | Adam Serwinowski# | 2 | 2025-2026 | |
| 9 | David Speer | 2 | 2019-2021 | |
| 9 | Louie Varland# | 2 | 2022-2023 | |
| 9 | Zack Wheeler# | 2 | 2013-2013 | |
| 9 | Thomas White# | 2 | 2025-2026 | |
| 30 | Andrew Albers | 1 | 2013-2015 | |
| 30 | Matt Andriese | 1 | 2014-2016 | |
| 30 | Shawn Armstrong# | 1 | 2014-2015 | |
| 30 | D.J. Baxendale | 1 | 2019-2019 | |
| 30 | Aaron Blair | 1 | 2016-2020 | |
| 30 | Denny Brady# | 1 | 2020-2021 | |
| 30 | Marc Brakeman | 1 | 2018-2021 | |
| 30 | Colten Brewer# | 1 | 2021-2024 | |
| 30 | Trace Bright# | 1 | 2025-2026 | |
| 30 | Tyler Brown# | 1 | 2023-2025 | |
| 30 | Dan Camarena# | 1 | 2022-2022 | |
| 30 | Moises Chace# | 1 | 2026-2026 | |
| 30 | Trevor Clifton# | 1 | 2020-2024 | |
| 30 | Tim Crabbe | 1 | 2015-2016 | |
| 30 | Malcolm Culver | 1 | 2016-2017 | |
| 30 | Xzavion Curry# | 1 | 2025-2025 | |
| 30 | Garrett Davila# | 1 | 2022-2025 | |
| 30 | Jose De Paula | 1 | 2013-2014 | |
| 30 | Josh Degraaf | 1 | 2019-2021 | |
| 30 | Ross Detwiler | 1 | 2016-2019 | |
| 30 | Jose Dicochea# | 1 | 2025-2026 | |
| 30 | Bobby Doran | 1 | 2013-2016 | |
| 30 | Kyle Drabek | 1 | 2017-2017 | |
| 30 | Jon Edwards | 1 | 2015-2021 | |
| 30 | Brandon Eisert# | 1 | 2025-2026 | |
| 30 | Luke Eubank | 1 | 2019-2021 | |
| 30 | Nelson Gonzalez | 1 | 2018-2019 | |
| 30 | Ashton Goudeau | 1 | 2017-2022 | |
| 30 | Reymin Guduan | 1 | 2019-2019 | |
| 30 | Angel Heredia | 1 | 2018-2019 | |
| 30 | James Hicks# | 1 | 2025-2025 | |
| 30 | Matt Hoffman | 1 | 2013-2015 | |
| 30 | J.J. Hoover | 1 | 2017-2019 | |
| 30 | Colt Hynes | 1 | 2014-2018 | |
| 30 | William Kelly | 1 | 2017-2017 | |
| 30 | Zak Kent# | 1 | 2026-2026 | |
| 30 | Dean Kiekhefer | 1 | 2014-2016 | |
| 30 | Stephen Kolek# | 1 | 2024-2025 | |
| 30 | Mark Lamm | 1 | 2014-2016 | |
| 30 | Justin Lange# | 1 | 2025-2025 | |
| 30 | David Leal# | 1 | 2022-2025 | |
| 30 | Joel Linares | 1 | 2016-2016 | |
| 30 | Grayson Long | 1 | 2017-2019 | |
| 30 | Daniel Lynch# | 1 | 2020-2021 | |
| 30 | Adam Maier# | 1 | 2025-2026 | |
| 30 | Joe Mantiply# | 1 | 2021-2021 | |
| 30 | Griff McGarry# | 1 | 2023-2024 | |
| 30 | John McMillon# | 1 | 2023-2025 | |
| 30 | Yoel Mecias | 1 | 2017-2018 | |
| 30 | Carson Montgomery# | 1 | 2026-2026 | |
| 30 | Sean Mooney# | 1 | 2022-2026 | |
| 30 | A.J. Morris | 1 | 2013-2017 | |
| 30 | Reese Olson# | 1 | 2022-2023 | |
| 30 | Andy Otero | 1 | 2022-2022 | |
| 30 | Carson Palmquist# | 1 | 2024-2025 | |
| 30 | Dylan Phillips# | 1 | 2024-2025 | |
| 30 | Ivan Pineyro | 1 | 2017-2017 | |
| 30 | Cal Quantrill# | 1 | 2019-2026 | |
| 30 | Andrew Quezada# | 1 | 2022-2024 | |
| 30 | Aldo Ramirez# | 1 | 2026-2026 | |
| 30 | Neil Ramirez | 1 | 2019-2019 | |
| 30 | Chris Reed | 1 | 2013-2021 | |
| 30 | Ethan Roberts# | 1 | 2025-2025 | |
| 30 | Manuel Rodriguez# | 1 | 2022-2024 | |
| 30 | Dalton Rogers# | 1 | 2026-2026 | |
| 30 | Enny Romero | 1 | 2019-2020 | |
| 30 | Joe Ross# | 1 | 2015-2015 | |
| 30 | Ramon Rosso# | 1 | 2020-2024 | |
| 30 | Frank Rubio | 1 | 2020-2021 | |
| 30 | Josh Sborz# | 1 | 2017-2023 | |
| 30 | Andrew Schultz# | 1 | 2020-2020 |
