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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Luis Gil# | 11 | 2020-2020 | |
| 2 | John Rooney# | 8 | 2020-2020 | |
| 3 | Ryan Dease# | 7 | 2020-2020 | |
| 3 | Chris McMahon# | 7 | 2020-2020 | |
| 3 | Erik Miller# | 7 | 2020-2020 | |
| 6 | Brandon Bailey# | 6 | 2020-2020 | |
| 6 | Cameron Burford# | 6 | 2020-2020 | |
| 6 | Beau Burrows# | 6 | 2020-2020 | |
| 6 | Yerelmy Garcia# | 6 | 2020-2020 | |
| 6 | Jacob Kush# | 6 | 2020-2020 | |
| 6 | Michael McAvene# | 6 | 2020-2020 | |
| 6 | Patrick Raby# | 6 | 2020-2020 | |
| 6 | Jonathan Stiever# | 6 | 2020-2020 | |
| 6 | Nick Wallerstedt# | 6 | 2020-2020 | |
| 15 | Hunter Barco# | 5 | 2020-2020 | |
| 15 | Jesse Bergin# | 5 | 2020-2020 | |
| 15 | Brandon Birdsell# | 5 | 2020-2020 | |
| 15 | Matt Brash# | 5 | 2020-2020 | |
| 15 | Sean Burke# | 5 | 2020-2020 | |
| 15 | Yordani Carmona# | 5 | 2020-2020 | |
| 15 | Cre Finfrock# | 5 | 2020-2020 | |
| 15 | Logan Forsythe# | 5 | 2020-2020 | |
| 15 | Colby Gomes# | 5 | 2020-2020 | |
| 15 | Jairo Lopez# | 5 | 2020-2020 | |
| 15 | Adam Lukas# | 5 | 2020-2020 | |
| 15 | Tommy Mace# | 5 | 2020-2020 | |
| 15 | Junior Mieses# | 5 | 2020-2020 | |
| 15 | Bobby Miller# | 5 | 2020-2020 | |
| 15 | Derek Molina# | 5 | 2020-2020 | |
| 15 | Gabriel Morales# | 5 | 2020-2020 | |
| 15 | Anderson Munoz# | 5 | 2020-2020 | |
| 15 | Dawson Netz# | 5 | 2020-2020 | |
| 15 | Garret Price# | 5 | 2020-2020 | |
| 15 | Antonio Sandoval# | 5 | 2020-2020 | |
| 15 | Andrew Schultz# | 5 | 2020-2020 | |
| 15 | Davis Sharpe# | 5 | 2020-2020 | |
| 15 | Jared Southard# | 5 | 2020-2020 | |
| 15 | Nick Steckel# | 5 | 2020-2020 | |
| 15 | Jonathan Stroman# | 5 | 2020-2020 | |
| 15 | Nick Thwaits# | 5 | 2020-2020 | |
| 15 | Cam Tringali# | 5 | 2020-2020 | |
| 15 | Ryan Zeferjahn# | 5 | 2020-2020 | |
| 43 | Yoan Aybar# | 4 | 2020-2020 | |
| 43 | Luke Bartnicki# | 4 | 2020-2020 | |
| 43 | Collin Bosley-Smith# | 4 | 2020-2020 | |
| 43 | Mike Bryant# | 4 | 2020-2020 | |
| 43 | Ryan Cabarcas# | 4 | 2020-2020 | |
| 43 | Andy Cheshier# | 4 | 2020-2020 | |
| 43 | Brayan De Paula# | 4 | 2020-2020 | |
| 43 | Jamie Dujardin# | 4 | 2020-2020 | |
| 43 | Jaylen Eichler# | 4 | 2020-2020 | |
| 43 | Breiling Eusebio# | 4 | 2020-2020 | |
| 43 | Dave Falco# | 4 | 2020-2020 | |
| 43 | Omar Fernandez# | 4 | 2020-2020 | |
| 43 | Christopher Gau# | 4 | 2020-2020 | |
| 43 | Albert Hernandez# | 4 | 2020-2020 | |
| 43 | Randon Hostert# | 4 | 2020-2020 | |
| 43 | John Humphrey# | 4 | 2020-2020 | |
| 43 | Zach Kohn# | 4 | 2020-2020 | |
| 43 | Nick Lee# | 4 | 2020-2020 | |
| 43 | Dylan Lesko# | 4 | 2020-2020 | |
| 43 | Christian Lothes# | 4 | 2020-2020 | |
| 43 | Alec Marsh# | 4 | 2020-2020 | |
| 43 | Randy McNees# | 4 | 2020-2020 | |
| 43 | Juan Mejia# | 4 | 2020-2020 | |
| 43 | Jose Montilla# | 4 | 2020-2020 | |
| 43 | Spencer Moran# | 4 | 2020-2020 | |
| 43 | Doug Nikhazy# | 4 | 2020-2020 | |
| 43 | Bryce Osmond# | 4 | 2020-2020 | |
| 43 | Jeremy Ovalle# | 4 | 2020-2020 | |
| 43 | Hunter Owen# | 4 | 2020-2020 | |
| 43 | Manny Ramirez# | 4 | 2020-2020 | |
| 43 | Matt Russell# | 4 | 2020-2020 | |
| 43 | Colin Schmid# | 4 | 2020-2020 | |
| 43 | Brett Schulze# | 4 | 2020-2020 | |
| 43 | Ricardo Serna# | 4 | 2020-2020 | |
| 43 | Loreto Siniscalchi# | 4 | 2020-2020 | |
| 43 | Scott Spring# | 4 | 2020-2020 | |
| 43 | Josh Stegall# | 4 | 2020-2020 | |
| 43 | Sean Sullivan# | 4 | 2020-2020 | |
| 43 | Evan Vanek# | 4 | 2020-2020 | |
| 43 | Nolan Watson# | 4 | 2020-2020 | |
| 43 | Josh Winder# | 4 | 2020-2020 | |
| 84 | Farmer Abendroth# | 3 | 2020-2020 | |
| 84 | Ben Anderson# | 3 | 2020-2020 | |
| 84 | Ernesto Borges# | 3 | 2020-2020 | |
| 84 | Julian Bosnic# | 3 | 2020-2020 | |
| 84 | Hunter Brown# | 3 | 2020-2020 | |
| 84 | Connor Bruce# | 3 | 2020-2020 | |
| 84 | Evan Butler# | 3 | 2020-2020 | |
| 84 | Brodie Chestnutt# | 3 | 2020-2020 | |
| 84 | Nick Chittum# | 3 | 2020-2020 | |
| 84 | Chris Clarke# | 3 | 2020-2020 | |
| 84 | Matt Cleveland# | 3 | 2020-2020 | |
| 84 | Maximo Cortes# | 3 | 2020-2020 | |
| 84 | Magdiel Cotto# | 3 | 2020-2020 | |
| 84 | Richie Dell# | 3 | 2020-2020 | |
| 84 | Andres Diaz# | 3 | 2020-2020 | |
| 84 | Jason Diaz# | 3 | 2020-2020 | |
| 84 | Joey Dixon# | 3 | 2020-2020 |
