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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 | Ty Blach# | 2 | 2014-2025 | |
| 6 | Buddy Boshers | 2 | 2016-2021 | |
| 6 | Hunter Brown# | 2 | 2022-2024 | |
| 6 | David Buchanan# | 2 | 2015-2021 | |
| 6 | Paul Campbell# | 2 | 2020-2025 | |
| 6 | Davis Daniel# | 2 | 2022-2025 | |
| 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 | Adrian M. Martinez# | 2 | 2023-2025 | |
| 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 | Jefry Rodriguez# | 2 | 2020-2025 | |
| 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 | |
| 31 | Scott Alexander# | 1 | 2014-2024 | |
| 31 | Jose Alvarez | 1 | 2015-2021 | |
| 31 | Spencer Arrighetti# | 1 | 2025-2025 | |
| 31 | Barrett Astin | 1 | 2017-2018 | |
| 31 | Chris Bassitt# | 1 | 2018-2018 | |
| 31 | Tristan Beck# | 1 | 2021-2025 | |
| 31 | Hayden Birdsong# | 1 | 2025-2025 | |
| 31 | Nolan Blackwood# | 1 | 2018-2022 | |
| 31 | Steven Brault | 1 | 2017-2021 | |
| 31 | Beau Brieske# | 1 | 2022-2024 | |
| 31 | Ben Brown# | 1 | 2023-2025 | |
| 31 | Madison Bumgarner | 1 | 2013-2013 | |
| 31 | Vicente Campos | 1 | 2018-2018 | |
| 31 | Will Carter | 1 | 2016-2020 | |
| 31 | Diego Castillo# | 1 | 2019-2025 | |
| 31 | Tim Cate# | 1 | 2022-2022 | |
| 31 | Xavier Cedeno | 1 | 2019-2021 | |
| 31 | Tyler Chatwood | 1 | 2014-2019 | |
| 31 | Shane Dawson | 1 | 2020-2021 | |
| 31 | Sean Doolittle | 1 | 2013-2013 | |
| 31 | Carl Edwards Jr.# | 1 | 2016-2017 | |
| 31 | Scott Elbert | 1 | 2014-2016 | |
| 31 | Luke Farrell# | 1 | 2020-2025 | |
| 31 | Neftali Feliz | 1 | 2016-2018 | |
| 31 | Kyle Freeland# | 1 | 2024-2025 | |
| 31 | Christian Friedrich | 1 | 2014-2021 | |
| 31 | Reed Garrett# | 1 | 2018-2024 | |
| 31 | Cory Gearrin | 1 | 2013-2020 | |
| 31 | Tyler Glasnow# | 1 | 2016-2021 | |
| 31 | Miguel Gonzalez | 1 | 2018-2018 | |
| 31 | Josiah Gray# | 1 | 2022-2025 | |
| 31 | Jordan Guerrero# | 1 | 2018-2020 | |
| 31 | Rich Hill# | 1 | 2013-2025 | |
| 31 | Cole Irvin# | 1 | 2025-2025 | |
| 31 | James Kaprielian# | 1 | 2021-2025 | |
| 31 | Casey Kelly# | 1 | 2021-2024 | |
| 31 | Joe Kelly# | 1 | 2015-2021 | |
| 31 | Merrill Kelly# | 1 | 2019-2025 | |
| 31 | Caleb Kilian# | 1 | 2022-2025 | |
| 31 | Tom Koehler | 1 | 2018-2021 | |
| 31 | Travis Lakins# | 1 | 2019-2024 | |
| 31 | Jimmy Lambert# | 1 | 2021-2024 | |
| 31 | Ben Lively# | 1 | 2014-2023 | |
| 31 | Grayson Long | 1 | 2018-2018 | |
| 31 | Jorge Lopez# | 1 | 2015-2020 | |
| 31 | Yunior Marte# | 1 | 2022-2025 | |
| 31 | Marcelo Martinez# | 1 | 2022-2025 | |
| 31 | Seth Martinez# | 1 | 2022-2025 | |
| 31 | Yuki Matsui# | 1 | 2024-2025 | |
| 31 | Casey Mize# | 1 | 2020-2022 | |
| 31 | Ricky Nolasco | 1 | 2016-2016 | |
| 31 | Jose Ortega | 1 | 2014-2017 | |
| 31 | Joseph Ortiz | 1 | 2013-2016 | |
| 31 | Josh Osich | 1 | 2015-2018 | |
| 31 | Max Povse | 1 | 2018-2021 | |
| 31 | Wilking Rodriguez# | 1 | 2017-2025 | |
| 31 | Tyler Rogers# | 1 | 2018-2019 | |
| 31 | Ryan Rolison# | 1 | 2022-2023 | |
| 31 | Tommy Romero# | 1 | 2022-2025 | |
| 31 | Drew Rucinski# | 1 | 2018-2025 | |
| 31 | Dennis Santana# | 1 | 2019-2024 | |
| 31 | Tyler Skaggs | 1 | 2014-2014 | |
| 31 | Smith Smith | 1 | 2013-2014 | |
| 31 | D.J. Snelten | 1 | 2018-2018 | |
| 31 | Marcus Stroman# | 1 | 2013-2025 | |
| 31 | Michael Tonkin# | 1 | 2014-2016 | |
| 31 | Sam Tuivailala | 1 | 2016-2016 | |
| 31 | Ryan Weber | 1 | 2016-2023 | |
| 31 | Zack Weiss# | 1 | 2023-2025 | |
| 31 | Rowan Wick# | 1 | 2020-2023 |
