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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Brian Bayliss | 3 | 2016-2016 | |
| 1 | Mason Erla# | 3 | 2023-2026 | |
| 1 | Tim Hill# | 3 | 2018-2024 | |
| 1 | Rhett Kouba# | 3 | 2025-2026 | |
| 1 | Charlie Shirek | 3 | 2013-2014 | |
| 1 | Anthony Solometo# | 3 | 2024-2025 | |
| 7 | Sean Brady | 2 | 2019-2021 | |
| 7 | Adrian Chaidez# | 2 | 2023-2026 | |
| 7 | Alex Cook# | 2 | 2024-2024 | |
| 7 | Matt Crouse | 2 | 2014-2016 | |
| 7 | Paul Demny | 2 | 2013-2016 | |
| 7 | Ricky DeVito# | 2 | 2022-2024 | |
| 7 | Scott Effross# | 2 | 2019-2021 | |
| 7 | Alex Faedo# | 2 | 2019-2021 | |
| 7 | Geoff Hartlieb# | 2 | 2018-2023 | |
| 7 | Thomas Hatch# | 2 | 2019-2019 | |
| 7 | Bryce Hubbart# | 2 | 2025-2026 | |
| 7 | George Kirby# | 2 | 2020-2021 | |
| 7 | Brendon Little# | 2 | 2018-2024 | |
| 7 | Will Mabrey# | 2 | 2024-2024 | |
| 7 | T.J. McFarland | 2 | 2017-2018 | |
| 7 | Wen-Hui Pan# | 2 | 2025-2026 | |
| 7 | Eury Perez# | 2 | 2023-2023 | |
| 7 | Tyler Pill | 2 | 2013-2022 | |
| 7 | Josh Prevost | 2 | 2016-2017 | |
| 7 | A.J. Puk# | 2 | 2018-2018 | |
| 7 | Montreal Robertson | 2 | 2015-2016 | |
| 7 | Jen-Ho Tseng | 2 | 2022-2023 | |
| 7 | Luis Ysla | 2 | 2015-2021 | |
| 30 | Scott Alexander# | 1 | 2016-2016 | |
| 30 | Dylan Baker | 1 | 2014-2023 | |
| 30 | Trey Ball | 1 | 2016-2019 | |
| 30 | Bryce Bandilla | 1 | 2014-2014 | |
| 30 | Peyton Battenfield# | 1 | 2022-2024 | |
| 30 | Caleb Beech | 1 | 2017-2017 | |
| 30 | Casey Bloomquist | 1 | 2016-2022 | |
| 30 | Ethan Bosacker# | 1 | 2026-2026 | |
| 30 | Hunter Breault# | 1 | 2023-2026 | |
| 30 | Tim Brennan# | 1 | 2021-2024 | |
| 30 | Parker Bridwell | 1 | 2014-2022 | |
| 30 | Jarrett Burgess | 1 | 2016-2016 | |
| 30 | Eric Carter | 1 | 2017-2019 | |
| 30 | Yeiper Castillo | 1 | 2017-2018 | |
| 30 | Mike Clevinger# | 1 | 2015-2015 | |
| 30 | Harrison Cooney | 1 | 2019-2019 | |
| 30 | Tyler Cravy | 1 | 2014-2015 | |
| 30 | Jose De Paula | 1 | 2013-2014 | |
| 30 | Ryan Eades | 1 | 2015-2017 | |
| 30 | Alex Fagalde | 1 | 2018-2022 | |
| 30 | Luke Farrell# | 1 | 2017-2023 | |
| 30 | Chris Flexen# | 1 | 2017-2017 | |
| 30 | Dax Fulton# | 1 | 2025-2025 | |
| 30 | Robert Gsellman | 1 | 2014-2016 | |
| 30 | Jason Gurka | 1 | 2013-2021 | |
| 30 | Jandel Gustave | 1 | 2015-2017 | |
| 30 | Tyler Herb | 1 | 2023-2023 | |
| 30 | Jefri Hernandez | 1 | 2014-2014 | |
| 30 | Tyler Higgins | 1 | 2016-2020 | |
| 30 | Robbie Hitt# | 1 | 2020-2024 | |
| 30 | Aaron Holiday# | 1 | 2023-2026 | |
| 30 | Bryan Hudson# | 1 | 2019-2020 | |
| 30 | John Kilichowski | 1 | 2018-2019 | |
| 30 | Franklyn Kilome# | 1 | 2020-2024 | |
| 30 | Lucas Knowles# | 1 | 2024-2025 | |
| 30 | Stephen Kolek# | 1 | 2021-2023 | |
| 30 | Will Latcham | 1 | 2019-2021 | |
| 30 | Adam Liberatore | 1 | 2013-2013 | |
| 30 | Tony Locey# | 1 | 2024-2025 | |
| 30 | Joshua Loeschorn# | 1 | 2024-2026 | |
| 30 | Jaron Long | 1 | 2019-2020 | |
| 30 | Austin Love# | 1 | 2022-2023 | |
| 30 | Luis Lugo# | 1 | 2017-2024 | |
| 30 | Christian MacLeod# | 1 | 2023-2023 | |
| 30 | Brennan Malone# | 1 | 2022-2025 | |
| 30 | Rafael Marcano# | 1 | 2024-2026 | |
| 30 | Easton Marks# | 1 | 2026-2026 | |
| 30 | Alec Marsh# | 1 | 2021-2021 | |
| 30 | Zach McCambley# | 1 | 2022-2024 | |
| 30 | Chris McElvain# | 1 | 2025-2026 | |
| 30 | Griff McGarry# | 1 | 2023-2025 | |
| 30 | Kyle McGowin# | 1 | 2018-2018 | |
| 30 | Mike Montgomery | 1 | 2013-2013 | |
| 30 | Brock Moore# | 1 | 2025-2026 | |
| 30 | Steve Naemark | 1 | 2017-2018 | |
| 30 | Sammy Natera# | 1 | 2024-2026 | |
| 30 | James Needy | 1 | 2017-2019 | |
| 30 | Jack O'Loughlin# | 1 | 2024-2025 | |
| 30 | Bryce Osmond# | 1 | 2024-2026 | |
| 30 | Brady Puckett# | 1 | 2022-2023 | |
| 30 | Cal Quantrill# | 1 | 2018-2019 | |
| 30 | Carson Ragsdale# | 1 | 2024-2024 | |
| 30 | Dylan Ray# | 1 | 2023-2025 | |
| 30 | Armando Rivero | 1 | 2015-2017 | |
| 30 | Donn Roach | 1 | 2015-2015 | |
| 30 | Leonardo A. Rodriguez# | 1 | 2021-2026 | |
| 30 | Wilking Rodriguez# | 1 | 2015-2021 | |
| 30 | Christian Romero# | 1 | 2024-2026 | |
| 30 | Joe Ross# | 1 | 2014-2015 | |
| 30 | Ben Rowen | 1 | 2015-2018 | |
| 30 | Logan Salow | 1 | 2019-2019 |
