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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Carlos Rodon# | 5 | 2016-2019 | |
| 2 | Josh James# | 4 | 2019-2020 | |
| 3 | Jake Kalish# | 3 | 2019-2023 | |
| 3 | Jordan Stephens | 3 | 2016-2024 | |
| 3 | Julio Teheran | 3 | 2013-2013 | |
| 6 | Brady Basso# | 2 | 2024-2024 | |
| 6 | Buddy Boshers | 2 | 2016-2021 | |
| 6 | Hunter Brown# | 2 | 2022-2024 | |
| 6 | David Buchanan# | 2 | 2015-2021 | |
| 6 | Robbie Erlin# | 2 | 2013-2018 | |
| 6 | Miguel A. Gonzalez | 2 | 2014-2018 | |
| 6 | MacKenzie Gore# | 2 | 2023-2024 | |
| 6 | Michael Grove# | 2 | 2023-2024 | |
| 6 | Jeremy Hefner | 2 | 2013-2017 | |
| 6 | Collin McHugh | 2 | 2013-2015 | |
| 6 | Alex Meyer | 2 | 2013-2017 | |
| 6 | Scott Moss | 2 | 2018-2024 | |
| 6 | Luis Perdomo# | 2 | 2017-2018 | |
| 6 | Roberto Perez | 2 | 2017-2017 | |
| 6 | Danny Salazar | 2 | 2014-2017 | |
| 6 | Cristopher Sanchez# | 2 | 2022-2024 | |
| 6 | Charlie Shirek | 2 | 2015-2016 | |
| 6 | Wander Suero# | 2 | 2018-2021 | |
| 6 | Jake Thompson | 2 | 2016-2020 | |
| 6 | Ryan Thompson# | 2 | 2020-2023 | |
| 26 | Scott Alexander# | 1 | 2014-2024 | |
| 26 | Jose Alvarez | 1 | 2015-2021 | |
| 26 | Barrett Astin | 1 | 2017-2018 | |
| 26 | Chris Bassitt# | 1 | 2018-2018 | |
| 26 | Tristan Beck# | 1 | 2021-2025 | |
| 26 | Nolan Blackwood# | 1 | 2018-2022 | |
| 26 | Steven Brault | 1 | 2017-2021 | |
| 26 | Beau Brieske# | 1 | 2022-2024 | |
| 26 | Ben Brown# | 1 | 2023-2025 | |
| 26 | Madison Bumgarner | 1 | 2013-2013 | |
| 26 | Paul Campbell# | 1 | 2020-2023 | |
| 26 | Vicente Campos | 1 | 2018-2018 | |
| 26 | Will Carter | 1 | 2016-2020 | |
| 26 | Tim Cate# | 1 | 2022-2022 | |
| 26 | Xavier Cedeno | 1 | 2019-2021 | |
| 26 | Tyler Chatwood | 1 | 2014-2019 | |
| 26 | Davis Daniel# | 1 | 2022-2025 | |
| 26 | Shane Dawson | 1 | 2020-2021 | |
| 26 | Sean Doolittle | 1 | 2013-2013 | |
| 26 | Carl Edwards Jr.# | 1 | 2016-2017 | |
| 26 | Scott Elbert | 1 | 2014-2016 | |
| 26 | Luke Farrell# | 1 | 2020-2022 | |
| 26 | Neftali Feliz | 1 | 2016-2018 | |
| 26 | Kyle Freeland# | 1 | 2024-2025 | |
| 26 | Christian Friedrich | 1 | 2014-2021 | |
| 26 | Reed Garrett# | 1 | 2018-2024 | |
| 26 | Cory Gearrin | 1 | 2013-2020 | |
| 26 | Tyler Glasnow# | 1 | 2016-2021 | |
| 26 | Miguel Gonzalez | 1 | 2018-2018 | |
| 26 | Josiah Gray# | 1 | 2022-2023 | |
| 26 | Jordan Guerrero# | 1 | 2018-2020 | |
| 26 | Rich Hill# | 1 | 2013-2025 | |
| 26 | James Kaprielian# | 1 | 2021-2025 | |
| 26 | Casey Kelly# | 1 | 2021-2024 | |
| 26 | Joe Kelly# | 1 | 2015-2021 | |
| 26 | Merrill Kelly# | 1 | 2019-2022 | |
| 26 | Caleb Kilian# | 1 | 2022-2025 | |
| 26 | Tom Koehler | 1 | 2018-2021 | |
| 26 | Travis Lakins# | 1 | 2019-2024 | |
| 26 | Jimmy Lambert# | 1 | 2021-2024 | |
| 26 | Ben Lively# | 1 | 2014-2023 | |
| 26 | Grayson Long | 1 | 2018-2018 | |
| 26 | Jorge Lopez# | 1 | 2015-2020 | |
| 26 | Adrian M. Martinez# | 1 | 2023-2025 | |
| 26 | Marcelo Martinez# | 1 | 2022-2025 | |
| 26 | Seth Martinez# | 1 | 2022-2025 | |
| 26 | Yuki Matsui# | 1 | 2024-2025 | |
| 26 | Casey Mize# | 1 | 2020-2022 | |
| 26 | Ricky Nolasco | 1 | 2016-2016 | |
| 26 | Jose Ortega | 1 | 2014-2017 | |
| 26 | Joseph Ortiz | 1 | 2013-2016 | |
| 26 | Josh Osich | 1 | 2015-2018 | |
| 26 | Max Povse | 1 | 2018-2021 | |
| 26 | Jefry Rodriguez# | 1 | 2020-2025 | |
| 26 | Wilking Rodriguez# | 1 | 2017-2025 | |
| 26 | Tyler Rogers# | 1 | 2018-2019 | |
| 26 | Ryan Rolison# | 1 | 2022-2023 | |
| 26 | Tommy Romero# | 1 | 2022-2025 | |
| 26 | Dennis Santana# | 1 | 2019-2024 | |
| 26 | Tyler Skaggs | 1 | 2014-2014 | |
| 26 | Smith Smith | 1 | 2013-2014 | |
| 26 | D.J. Snelten | 1 | 2018-2018 | |
| 26 | Marcus Stroman# | 1 | 2013-2016 | |
| 26 | Michael Tonkin# | 1 | 2014-2016 | |
| 26 | Sam Tuivailala | 1 | 2016-2016 | |
| 26 | Ryan Weber | 1 | 2016-2023 | |
| 26 | Zack Weiss# | 1 | 2023-2024 | |
| 26 | Rowan Wick# | 1 | 2020-2023 | |
| 26 | Brad Wieck# | 1 | 2017-2020 | |
| 26 | Taylor Williams | 1 | 2018-2020 | |
| 26 | Blake Wood | 1 | 2019-2020 | |
| 26 | Steven Wright | 1 | 2015-2021 | |
| 26 | Ryan Yarbrough# | 1 | 2015-2020 | |
| 26 | Angel Zerpa# | 1 | 2024-2025 | |
| 100 | Andury Acevedo | 0 | 2016-2021 |
