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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 | Tim Hill# | 3 | 2018-2024 | |
| 1 | Charlie Shirek | 3 | 2013-2014 | |
| 1 | Anthony Solometo# | 3 | 2024-2025 | |
| 5 | Sean Brady | 2 | 2019-2021 | |
| 5 | Alex Cook# | 2 | 2024-2024 | |
| 5 | Matt Crouse | 2 | 2014-2016 | |
| 5 | Paul Demny | 2 | 2013-2016 | |
| 5 | Ricky DeVito# | 2 | 2022-2024 | |
| 5 | Scott Effross# | 2 | 2019-2021 | |
| 5 | Alex Faedo# | 2 | 2019-2021 | |
| 5 | Geoff Hartlieb# | 2 | 2018-2023 | |
| 5 | Thomas Hatch# | 2 | 2019-2019 | |
| 5 | George Kirby# | 2 | 2020-2021 | |
| 5 | Rhett Kouba# | 2 | 2025-2025 | |
| 5 | Brendon Little# | 2 | 2018-2024 | |
| 5 | Will Mabrey# | 2 | 2024-2024 | |
| 5 | T.J. McFarland | 2 | 2017-2018 | |
| 5 | Eury Perez# | 2 | 2023-2023 | |
| 5 | Tyler Pill | 2 | 2013-2022 | |
| 5 | Josh Prevost | 2 | 2016-2017 | |
| 5 | A.J. Puk# | 2 | 2018-2018 | |
| 5 | Montreal Robertson | 2 | 2015-2016 | |
| 5 | Jen-Ho Tseng | 2 | 2022-2023 | |
| 5 | Luis Ysla | 2 | 2015-2021 | |
| 26 | Scott Alexander# | 1 | 2016-2016 | |
| 26 | Dylan Baker | 1 | 2014-2023 | |
| 26 | Trey Ball | 1 | 2016-2019 | |
| 26 | Bryce Bandilla | 1 | 2014-2014 | |
| 26 | Peyton Battenfield# | 1 | 2022-2024 | |
| 26 | Caleb Beech | 1 | 2017-2017 | |
| 26 | Casey Bloomquist | 1 | 2016-2022 | |
| 26 | Hunter Breault# | 1 | 2023-2025 | |
| 26 | Tim Brennan# | 1 | 2021-2024 | |
| 26 | Parker Bridwell | 1 | 2014-2022 | |
| 26 | Jarrett Burgess | 1 | 2016-2016 | |
| 26 | Eric Carter | 1 | 2017-2019 | |
| 26 | Yeiper Castillo | 1 | 2017-2018 | |
| 26 | Adrian Chaidez# | 1 | 2023-2025 | |
| 26 | Mike Clevinger# | 1 | 2015-2015 | |
| 26 | Harrison Cooney | 1 | 2019-2019 | |
| 26 | Tyler Cravy | 1 | 2014-2015 | |
| 26 | Jose De Paula | 1 | 2013-2014 | |
| 26 | Ryan Eades | 1 | 2015-2017 | |
| 26 | Mason Erla# | 1 | 2023-2023 | |
| 26 | Alex Fagalde | 1 | 2018-2022 | |
| 26 | Luke Farrell# | 1 | 2017-2023 | |
| 26 | Chris Flexen# | 1 | 2017-2017 | |
| 26 | Dax Fulton# | 1 | 2025-2025 | |
| 26 | Robert Gsellman | 1 | 2014-2016 | |
| 26 | Jason Gurka | 1 | 2013-2021 | |
| 26 | Jandel Gustave# | 1 | 2015-2017 | |
| 26 | Tyler Herb | 1 | 2023-2023 | |
| 26 | Jefri Hernandez | 1 | 2014-2014 | |
| 26 | Tyler Higgins | 1 | 2016-2020 | |
| 26 | Robbie Hitt# | 1 | 2020-2024 | |
| 26 | Aaron Holiday# | 1 | 2023-2025 | |
| 26 | Bryan Hudson# | 1 | 2019-2020 | |
| 26 | John Kilichowski | 1 | 2018-2019 | |
| 26 | Franklyn Kilome# | 1 | 2020-2024 | |
| 26 | Lucas Knowles# | 1 | 2024-2025 | |
| 26 | Stephen Kolek# | 1 | 2021-2023 | |
| 26 | Will Latcham | 1 | 2019-2021 | |
| 26 | Adam Liberatore | 1 | 2013-2013 | |
| 26 | Tony Locey# | 1 | 2024-2025 | |
| 26 | Jaron Long | 1 | 2019-2020 | |
| 26 | Austin Love# | 1 | 2022-2023 | |
| 26 | Luis Lugo# | 1 | 2017-2024 | |
| 26 | Christian MacLeod# | 1 | 2023-2023 | |
| 26 | Brennan Malone# | 1 | 2022-2025 | |
| 26 | Rafael Marcano# | 1 | 2024-2025 | |
| 26 | Alec Marsh# | 1 | 2021-2021 | |
| 26 | Zach McCambley# | 1 | 2022-2024 | |
| 26 | Griff McGarry# | 1 | 2023-2025 | |
| 26 | Kyle McGowin# | 1 | 2018-2018 | |
| 26 | Mike Montgomery | 1 | 2013-2013 | |
| 26 | Brock Moore# | 1 | 2025-2025 | |
| 26 | Steve Naemark | 1 | 2017-2018 | |
| 26 | Sammy Natera# | 1 | 2024-2024 | |
| 26 | James Needy | 1 | 2017-2019 | |
| 26 | Jack O'Loughlin# | 1 | 2024-2025 | |
| 26 | Wen-Hui Pan# | 1 | 2025-2025 | |
| 26 | Brady Puckett# | 1 | 2022-2023 | |
| 26 | Cal Quantrill# | 1 | 2018-2019 | |
| 26 | Carson Ragsdale# | 1 | 2024-2024 | |
| 26 | Dylan Ray# | 1 | 2023-2025 | |
| 26 | Armando Rivero | 1 | 2015-2017 | |
| 26 | Donn Roach | 1 | 2015-2015 | |
| 26 | Leonardo A. Rodriguez# | 1 | 2021-2025 | |
| 26 | Wilking Rodriguez# | 1 | 2015-2021 | |
| 26 | Joe Ross# | 1 | 2014-2015 | |
| 26 | Ben Rowen | 1 | 2015-2018 | |
| 26 | Logan Salow | 1 | 2019-2019 | |
| 26 | Gonzalo Sanudo | 1 | 2017-2018 | |
| 26 | Matt Sauer# | 1 | 2022-2022 | |
| 26 | Noah Schultz# | 1 | 2025-2025 | |
| 26 | Robby Snelling# | 1 | 2024-2025 | |
| 26 | John Stilson | 1 | 2013-2018 | |
| 26 | Andrew Summerville | 1 | 2018-2021 | |
| 26 | Nicholas Tepesch | 1 | 2013-2013 |
