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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Postseason Career Leaderboard |
|---|---|---|---|---|
| 1 | Matt Sauer# | 1.000 | 2022 | |
| 1 | Charlie Shirek | 1.000 | 2014 | |
| 1 | Paul Demny | 1.000 | 2016 | |
| 1 | Cal Quantrill# | 1.000 | 2018 | |
| 1 | Ricky DeVito# | 1.000 | 2022 | |
| 1 | Josh Prevost | 1.000 | 2017 | |
| 1 | Trey Ball | 1.000 | 2016 | |
| 1 | John Stilson | 1.000 | 2013 | |
| 1 | Shane Watson | 1.000 | 2016 | |
| 1 | Casey Bloomquist | 1.000 | 2016 | |
| 1 | Joe Ross# | 1.000 | 2014 | |
| 1 | Bryce Hubbart# | 1.000 | 2026 | |
| 13 | Eury Perez# | .667 | 2023 | |
| 13 | Luis Ysla | .667 | 2015 | |
| 13 | Matt Crouse | .667 | 2015 | |
| 13 | Anthony Solometo# | .667 | 2024 | |
| 17 | Mike Clevinger# | .500 | 2015 | |
| 17 | Donn Roach | .500 | 2015 | |
| 17 | Nicholas Tepesch | .500 | 2013 | |
| 17 | Bryan Hudson# | .500 | 2019 | |
| 17 | Griff McGarry# | .500 | 2023 | |
| 17 | Rhett Kouba# | .500 | 2026 | |
| 17 | Zach McCambley# | .500 | 2023 | |
| 24 | Bryce Bandilla | .333 | 2014 | |
| 24 | Jake Wong# | .333 | 2021 | |
| 26 | Jesse Beal | .000 | 2016 | |
| 26 | Dan Reynolds | .000 | 2015 | |
| 26 | Sean Harney# | .000 | 2024 |
