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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Craig Breakfield# | 23 | 2022-2026 | |
| 2 | Danny Heasley# | 22 | 2021-2025 | |
| 2 | Omar Valentin# | 22 | 2017-2021 | |
| 4 | Jaden Mack# | 21 | 2013-2017 | |
| 5 | Josh Boyd# | 19 | 2022-2026 | |
| 5 | Lance Goecker# | 19 | 2013-2017 | |
| 5 | Dave Gulbranson# | 19 | 2022-2026 | |
| 5 | Dan Vatalaro# | 19 | 2022-2026 | |
| 9 | Steve Esquivel# | 17 | 2021-2025 | |
| 9 | Armando Flores | 17 | 2013-2017 | |
| 9 | Adam Noland# | 17 | 2019-2022 | |
| 9 | Mike Riddle# | 17 | 2022-2026 | |
| 9 | Josh Spratt# | 17 | 2023-2026 | |
| 14 | Cody Fields# | 16 | 2017-2021 | |
| 14 | Justin Hesley# | 16 | 2016-2020 | |
| 14 | Nick Horrocks# | 16 | 2013-2017 | |
| 14 | Brian Hughes# | 16 | 2014-2018 | |
| 14 | Keith O'Brien# | 16 | 2022-2026 | |
| 14 | Braden Shaw# | 16 | 2012-2016 | |
| 14 | Austin Sternberg# | 16 | 2022-2026 | |
| 14 | Mitch Wojciechowski# | 16 | 2017-2021 | |
| 22 | Rob Alvarez# | 15 | 2017-2021 | |
| 22 | Jerry Bowman# | 15 | 2013-2017 | |
| 22 | Andrew Braden# | 15 | 2017-2021 | |
| 22 | Julian Bryant# | 15 | 2012-2016 | |
| 22 | Joe Carver# | 15 | 2019-2023 | |
| 22 | Bill Clark | 15 | 2017-2021 | |
| 22 | Jim Dell# | 15 | 2023-2026 | |
| 22 | Allen Ellingson# | 15 | 2021-2025 | |
| 22 | Eric Ellington# | 15 | 2021-2025 | |
| 22 | Kevin Farris# | 15 | 2014-2018 | |
| 22 | Brian Gay# | 15 | 2015-2019 | |
| 22 | Rick Hill# | 15 | 2013-2017 | |
| 22 | John Manship# | 15 | 2016-2020 | |
| 22 | Jonathan Marich# | 15 | 2006-2009 | |
| 22 | Mike Winchester# | 15 | 2021-2025 | |
| 37 | Dane Baker# | 14 | 2021-2025 | |
| 37 | Dave Combs# | 14 | 2013-2017 | |
| 37 | Aaron Conklin# | 14 | 2018-2022 | |
| 37 | Branden Covington# | 14 | 2017-2021 | |
| 37 | Jason Emary# | 14 | 2016-2020 | |
| 37 | Pete Esposito | 14 | 2001-2002 | |
| 37 | Ken Fox | 14 | 2015-2018 | |
| 37 | Jon Goldman | 14 | 2007-2009 | |
| 37 | Ed Gonell# | 14 | 2022-2025 | |
| 37 | Jordan Green# | 14 | 2017-2020 | |
| 37 | Ahmed Harris | 14 | 2013-2017 | |
| 37 | Mike Hietala | 14 | 2012-2016 | |
| 37 | Scott Lewandowski# | 14 | 2021-2024 | |
| 37 | Tony Magallon# | 14 | 2021-2025 | |
| 37 | Andy Merrick# | 14 | 2021-2025 | |
| 37 | Brian Murray# | 14 | 2021-2025 | |
| 37 | Brad Porretta# | 14 | 2018-2021 | |
| 37 | Ryan Roeser# | 14 | 2015-2019 | |
| 37 | Marcos Rosas# | 14 | 2012-2016 | |
| 37 | Danny Sarinana | 14 | 2014-2018 | |
| 37 | Jason Schneider | 14 | 2013-2017 | |
| 37 | Aaron Trede# | 14 | 2022-2026 | |
| 37 | Joe Valance# | 14 | 2023-2026 | |
| 60 | Mike Ackerman# | 13 | 2018-2022 | |
| 60 | Dave Anderson# | 13 | 2017-2021 | |
| 60 | Myung-joo Au | 13 | 2013-2017 | |
| 60 | Danny Brabson | 13 | 2014-2018 | |
| 60 | Jason Brokaw | 13 | 2013-2017 | |
| 60 | Byron Bruce# | 13 | 2020-2024 | |
| 60 | Gil Carroll# | 13 | 2021-2025 | |
| 60 | Jon Champagne# | 13 | 2016-2020 | |
| 60 | Scott Chrysler# | 13 | 2020-2024 | |
| 60 | Rick Collins# | 13 | 2013-2016 | |
| 60 | Marcus Cornock# | 13 | 2022-2026 | |
| 60 | Ian Doty | 13 | 2008-2011 | |
| 60 | Colin Esser# | 13 | 2013-2016 | |
| 60 | Chris Furr | 13 | 2009-2012 | |
| 60 | Justin Gelineau# | 13 | 2023-2026 | |
| 60 | Pat Hanson# | 13 | 2019-2023 | |
| 60 | Michael Harkins# | 13 | 2021-2025 | |
| 60 | John Hennig# | 13 | 2016-2019 | |
| 60 | Cameron Joseph# | 13 | 2022-2026 | |
| 60 | Mike Kluttz# | 13 | 2013-2017 | |
| 60 | Eric Kretzer# | 13 | 2022-2025 | |
| 60 | Nestor Malyutkin# | 13 | 2021-2025 | |
| 60 | Logan Mayhew# | 13 | 2014-2018 | |
| 60 | Ryan McEntyre# | 13 | 2018-2022 | |
| 60 | Angel Morales# | 13 | 2013-2016 | |
| 60 | Jim Murphy# | 13 | 2017-2021 | |
| 60 | Dusty Nelson# | 13 | 2016-2020 | |
| 60 | Ken Phillips# | 13 | 2022-2025 | |
| 60 | Gray Price# | 13 | 2024-2026 | |
| 60 | Nate Ray# | 13 | 2015-2019 | |
| 60 | Earl Rushton# | 13 | 2022-2026 | |
| 60 | Brad Scioli# | 13 | 2022-2025 | |
| 60 | Ed Senter# | 13 | 2022-2026 | |
| 60 | Zachery Shaw# | 13 | 2020-2024 | |
| 60 | Jeremy Stewart# | 13 | 2020-2024 | |
| 60 | Ted Tygart# | 13 | 2012-2015 | |
| 60 | Dusty Walkey# | 13 | 2023-2026 | |
| 60 | Andy Waring# | 13 | 2013-2017 | |
| 60 | Paul Williamson# | 13 | 2012-2016 | |
| 99 | Jeremy Adams | 12 | 2014-2017 | |
| 99 | Angel Beas# | 12 | 2023-2026 |
