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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Brett Cecil | 4 | 2013-2013 | |
| 2 | Brent Honeywell Jr.# | 3 | 2018-2020 | |
| 2 | Corbin Martin# | 3 | 2019-2024 | |
| 2 | Luke Weaver# | 3 | 2017-2024 | |
| 5 | Alex Cobb# | 2 | 2013-2013 | |
| 5 | Jarred Cosart | 2 | 2013-2018 | |
| 5 | Paolo Espino# | 2 | 2016-2024 | |
| 5 | Giovanny Gallegos# | 2 | 2018-2018 | |
| 5 | John Gast | 2 | 2013-2017 | |
| 5 | David Hernandez | 2 | 2015-2021 | |
| 5 | Chase Johnson | 2 | 2020-2023 | |
| 5 | Nicholas Kingham | 2 | 2014-2015 | |
| 5 | Brandon Leibrandt# | 2 | 2018-2023 | |
| 5 | A.J. Minter# | 2 | 2018-2020 | |
| 5 | Kevin Quackenbush | 2 | 2016-2019 | |
| 5 | Brooks Raley# | 2 | 2014-2024 | |
| 5 | Ben Rowen | 2 | 2014-2015 | |
| 5 | Miguel Socolovich | 2 | 2017-2021 | |
| 5 | Chris Volstad | 2 | 2013-2021 | |
| 5 | Andrew Wantz# | 2 | 2024-2025 | |
| 5 | Gabriel Ynoa | 2 | 2016-2018 | |
| 22 | Tyler Alexander# | 1 | 2021-2025 | |
| 22 | Harold Arauz | 1 | 2018-2019 | |
| 22 | Jake Arrieta | 1 | 2013-2020 | |
| 22 | Tanner Bibee# | 1 | 2023-2023 | |
| 22 | Jesse Biddle | 1 | 2015-2024 | |
| 22 | Osvaldo Bido# | 1 | 2022-2025 | |
| 22 | Jeff Brigham# | 1 | 2020-2025 | |
| 22 | Rex Brothers | 1 | 2013-2018 | |
| 22 | Ryan Buchter | 1 | 2014-2022 | |
| 22 | Alan Busenitz | 1 | 2018-2021 | |
| 22 | Jared Carkuff | 1 | 2020-2022 | |
| 22 | Kyle Crockett | 1 | 2019-2021 | |
| 22 | Austin Davis# | 1 | 2019-2023 | |
| 22 | Rubby de la Rosa# | 1 | 2014-2015 | |
| 22 | Randall Delgado | 1 | 2013-2017 | |
| 22 | Nathan Eovaldi# | 1 | 2013-2015 | |
| 22 | Caleb Ferguson# | 1 | 2019-2022 | |
| 22 | Dylan File# | 1 | 2020-2025 | |
| 22 | Jack Flaherty# | 1 | 2018-2022 | |
| 22 | Brian Flynn | 1 | 2014-2021 | |
| 22 | Kody Funderburk# | 1 | 2024-2025 | |
| 22 | Shane Greene | 1 | 2015-2022 | |
| 22 | Jorge Guzman# | 1 | 2019-2019 | |
| 22 | Emerson Hancock# | 1 | 2023-2024 | |
| 22 | Brent Headrick# | 1 | 2023-2025 | |
| 22 | Andrew Heaney# | 1 | 2015-2018 | |
| 22 | Tommy Henry# | 1 | 2022-2024 | |
| 22 | Tim Herrin# | 1 | 2024-2024 | |
| 22 | Codi Heuer# | 1 | 2021-2022 | |
| 22 | Rich Hill# | 1 | 2024-2024 | |
| 22 | Sean Hjelle# | 1 | 2024-2025 | |
| 22 | T.J. House | 1 | 2015-2017 | |
| 22 | Wei-Chuah Huang# | 1 | 2023-2025 | |
| 22 | Jakob Junis# | 1 | 2024-2024 | |
| 22 | Janson Junk# | 1 | 2022-2024 | |
| 22 | Rob Kaminsky | 1 | 2020-2022 | |
| 22 | James Kaprielian# | 1 | 2018-2020 | |
| 22 | Brett Kennedy# | 1 | 2019-2023 | |
| 22 | Kwang-hyun Kim# | 1 | 2023-2025 | |
| 22 | Joseph Krehbiel# | 1 | 2019-2024 | |
| 22 | Jake Latz# | 1 | 2022-2024 | |
| 22 | Jonathan Loaisiga# | 1 | 2019-2020 | |
| 22 | Barret Loux | 1 | 2014-2016 | |
| 22 | Jordan Lyles# | 1 | 2014-2018 | |
| 22 | Alek Manoah# | 1 | 2021-2024 | |
| 22 | Brian Matusz | 1 | 2013-2016 | |
| 22 | Cory Mazzoni | 1 | 2018-2021 | |
| 22 | Daniel McCutchen | 1 | 2013-2017 | |
| 22 | Adalberto Mejia | 1 | 2018-2021 | |
| 22 | Wade Miley# | 1 | 2021-2021 | |
| 22 | Shelby Miller# | 1 | 2019-2025 | |
| 22 | Hoby Milner# | 1 | 2016-2020 | |
| 22 | Rafael Montero# | 1 | 2016-2025 | |
| 22 | Mark Montgomery | 1 | 2015-2021 | |
| 22 | Tobias Myers# | 1 | 2024-2025 | |
| 22 | Nick Nelson# | 1 | 2022-2025 | |
| 22 | Juan Nicasio | 1 | 2013-2023 | |
| 22 | Jacob Nix# | 1 | 2019-2023 | |
| 22 | Riley O'Brien# | 1 | 2021-2025 | |
| 22 | Lester Oliveros | 1 | 2013-2015 | |
| 22 | Chris Paddack# | 1 | 2019-2020 | |
| 22 | Thomas Pannone# | 1 | 2018-2018 | |
| 22 | Willy Paredes | 1 | 2016-2016 | |
| 22 | Manny Parra | 1 | 2014-2016 | |
| 22 | Wes Parsons | 1 | 2020-2021 | |
| 22 | Jack Patterson | 1 | 2020-2020 | |
| 22 | Red Patterson | 1 | 2013-2016 | |
| 22 | James Pazos | 1 | 2016-2022 | |
| 22 | Brad Peacock | 1 | 2017-2017 | |
| 22 | David Peterson# | 1 | 2020-2024 | |
| 22 | Clayton Richard | 1 | 2013-2017 | |
| 22 | Tom Robson | 1 | 2018-2021 | |
| 22 | Tekoah Roby# | 1 | 2024-2024 | |
| 22 | Chad Rogers | 1 | 2015-2016 | |
| 22 | Kyle Ryan | 1 | 2021-2023 | |
| 22 | Edgar Santana | 1 | 2018-2020 | |
| 22 | Jesse Scholtens# | 1 | 2022-2025 | |
| 22 | Paul Sewald# | 1 | 2018-2018 | |
| 22 | Braden Shipley | 1 | 2017-2024 |
