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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Jason Hursh | 3 | 2014-2020 | |
| 1 | Chris Martin# | 3 | 2016-2020 | |
| 1 | Colton Murray | 3 | 2017-2017 | |
| 1 | Thomas Szapucki# | 3 | 2018-2022 | |
| 5 | Anfernee Benitez | 2 | 2018-2018 | |
| 5 | Genesis Cabrera# | 2 | 2019-2021 | |
| 5 | Carlos Contreras | 2 | 2014-2017 | |
| 5 | Austin Cox# | 2 | 2020-2025 | |
| 5 | Tyler Cyr | 2 | 2018-2023 | |
| 5 | Austin Davis# | 2 | 2019-2025 | |
| 5 | Ben Joyce# | 2 | 2024-2024 | |
| 5 | Tom Koehler | 2 | 2018-2020 | |
| 5 | Nick Martinez# | 2 | 2014-2020 | |
| 5 | Frankie Montas# | 2 | 2015-2017 | |
| 5 | Doug Nikhazy# | 2 | 2023-2025 | |
| 5 | Luis Ortiz# | 2 | 2018-2019 | |
| 5 | Sammy Peralta# | 2 | 2024-2025 | |
| 5 | Donn Roach | 2 | 2014-2016 | |
| 5 | William Roberts | 2 | 2015-2017 | |
| 5 | Misael Siverio | 2 | 2016-2018 | |
| 5 | Ryne Slack | 2 | 2016-2021 | |
| 5 | Jordan Yamamoto# | 2 | 2016-2023 | |
| 23 | Austin Adams | 1 | 2013-2013 | |
| 23 | Blake Adams# | 1 | 2025-2025 | |
| 23 | Zach Agnos# | 1 | 2025-2025 | |
| 23 | Isaac Anderson | 1 | 2016-2019 | |
| 23 | Alec Asher | 1 | 2016-2016 | |
| 23 | Pedro Avila# | 1 | 2019-2021 | |
| 23 | Jeff Bain# | 1 | 2019-2025 | |
| 23 | Matt Ball | 1 | 2021-2022 | |
| 23 | Travis Ballew | 1 | 2016-2017 | |
| 23 | Kyle Bartsch | 1 | 2017-2017 | |
| 23 | Peyton Battenfield# | 1 | 2022-2025 | |
| 23 | Eric Berger | 1 | 2014-2016 | |
| 23 | Aaron Brooks | 1 | 2016-2019 | |
| 23 | Gaither Bumgardner | 1 | 2015-2016 | |
| 23 | Tanner Burns# | 1 | 2023-2024 | |
| 23 | Jared Carkuff | 1 | 2018-2019 | |
| 23 | Irv Carter# | 1 | 2022-2022 | |
| 23 | John Carver# | 1 | 2024-2024 | |
| 23 | Diego Castillo# | 1 | 2018-2018 | |
| 23 | Maximo Castillo# | 1 | 2022-2024 | |
| 23 | Shao-Ching Chiang | 1 | 2021-2021 | |
| 23 | Bailey Clark | 1 | 2020-2020 | |
| 23 | Garrett Cleavinger# | 1 | 2017-2022 | |
| 23 | Kyle Crick# | 1 | 2015-2017 | |
| 23 | Jeff Criswell# | 1 | 2023-2025 | |
| 23 | Coleman Crow# | 1 | 2022-2022 | |
| 23 | Wil Crowe# | 1 | 2020-2023 | |
| 23 | Brett De Geus# | 1 | 2025-2025 | |
| 23 | Yennsy Diaz# | 1 | 2020-2025 | |
| 23 | Jake Eder# | 1 | 2023-2025 | |
| 23 | Alex Faedo# | 1 | 2020-2021 | |
| 23 | Brady Feigl# | 1 | 2019-2025 | |
| 23 | Conor Fisk | 1 | 2018-2020 | |
| 23 | Patrick Francescon | 1 | 2016-2016 | |
| 23 | Percy Garner | 1 | 2014-2016 | |
| 23 | Cory Gearrin | 1 | 2019-2021 | |
| 23 | Sean Gilmartin | 1 | 2019-2023 | |
| 23 | Chad Girodo | 1 | 2017-2018 | |
| 23 | Anthony Gose# | 1 | 2022-2022 | |
| 23 | Preston Guilmet | 1 | 2017-2017 | |
| 23 | Alec Hansen | 1 | 2019-2021 | |
| 23 | Drew Harrington | 1 | 2018-2022 | |
| 23 | Kyle Harrison# | 1 | 2023-2025 | |
| 23 | Jon Heasley# | 1 | 2022-2023 | |
| 23 | Cole Henry# | 1 | 2023-2025 | |
| 23 | Ronald Herrera# | 1 | 2017-2025 | |
| 23 | Gunnar Hoglund# | 1 | 2023-2025 | |
| 23 | Grant Holman# | 1 | 2023-2025 | |
| 23 | Gregory Infante | 1 | 2013-2017 | |
| 23 | Steven Johnson | 1 | 2013-2017 | |
| 23 | Felix Jorge | 1 | 2016-2021 | |
| 23 | Jon Keller | 1 | 2017-2021 | |
| 23 | Logan Kensing | 1 | 2015-2016 | |
| 23 | Blaine Knight# | 1 | 2023-2025 | |
| 23 | Randy LeBlanc | 1 | 2018-2019 | |
| 23 | Barret Loux | 1 | 2015-2015 | |
| 23 | Matthew Lujan | 1 | 2017-2017 | |
| 23 | Ron Marinaccio# | 1 | 2023-2023 | |
| 23 | Whit Mayberry | 1 | 2017-2017 | |
| 23 | Kevin McCarthy | 1 | 2015-2022 | |
| 23 | Aaron McGarity# | 1 | 2022-2025 | |
| 23 | Andrew Misiaszek# | 1 | 2023-2025 | |
| 23 | Mark Montgomery | 1 | 2013-2015 | |
| 23 | Brian Moran# | 1 | 2013-2024 | |
| 23 | Penn Murfee# | 1 | 2024-2024 | |
| 23 | Jayden Murray# | 1 | 2023-2025 | |
| 23 | Nick Neidert# | 1 | 2019-2025 | |
| 23 | Trey Nielsen | 1 | 2017-2017 | |
| 23 | Sean Nolin | 1 | 2013-2015 | |
| 23 | Colin O'Connell | 1 | 2016-2016 | |
| 23 | Nate Ocker# | 1 | 2024-2025 | |
| 23 | Fernery Ozuna# | 1 | 2024-2025 | |
| 23 | Zach Peek# | 1 | 2022-2025 | |
| 23 | Luis Perdomo# | 1 | 2021-2025 | |
| 23 | Jean Pinto# | 1 | 2023-2025 | |
| 23 | A.J. Puckett# | 1 | 2017-2025 | |
| 23 | Matt Pushard# | 1 | 2025-2025 | |
| 23 | Lane Ramsey# | 1 | 2024-2024 |
