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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Andy Weatherholt# | 18 | 2019-2021 | |
| 2 | Ken Bixby# | 17 | 2015-2019 | |
| 3 | Roger Froehlich | 16 | 2012-2016 | |
| 3 | Rick Winkler# | 16 | 2013-2018 | |
| 5 | Antonio Alvarez# | 15 | 2018-2020 | |
| 5 | Andy Firkins | 15 | 2015-2018 | |
| 7 | Mike Arnerich# | 14 | 2012-2016 | |
| 7 | Nick Horrocks# | 14 | 2018-2021 | |
| 7 | Gil Martinez# | 14 | 2016-2018 | |
| 10 | Daniel Beckles# | 13 | 2016-2017 | |
| 10 | Donny Bisesi# | 13 | 2018-2020 | |
| 10 | Tony Casablanca# | 13 | 2017-2021 | |
| 10 | Jesus Fernandez# | 13 | 2012-2016 | |
| 10 | Jim Mendoza# | 13 | 2018-2020 | |
| 15 | Jose Contreras# | 12 | 2016-2018 | |
| 15 | Kareem Craig# | 12 | 2018-2021 | |
| 15 | Antonio Enriquez# | 12 | 2013-2016 | |
| 15 | Steve Gaucher# | 12 | 2012-2015 | |
| 15 | Mauricio Martinez# | 12 | 2014-2018 | |
| 15 | Chris Simon# | 12 | 2017-2020 | |
| 21 | Jerome Abney# | 11 | 2020-2021 | |
| 21 | Dennis Allen# | 11 | 2019-2020 | |
| 21 | Robby Brown | 11 | 2012-2016 | |
| 21 | Mike Canales# | 11 | 2013-2019 | |
| 21 | Rodrigo Gaeta | 11 | 2013-2017 | |
| 21 | Josh Hamilton# | 11 | 2017-2020 | |
| 21 | Rich Mack# | 11 | 2020-2021 | |
| 21 | Joe McLaughlin# | 11 | 2019-2021 | |
| 21 | Jose Perez# | 11 | 2020-2021 | |
| 21 | Matt Robinson | 11 | 2012-2017 | |
| 21 | Juan Sauceda | 11 | 2014-2018 | |
| 32 | Juan Barron# | 10 | 2014-2018 | |
| 32 | Brad Bixby# | 10 | 2016-2021 | |
| 32 | Mike Bryan# | 10 | 2013-2018 | |
| 32 | Adrian Capell | 10 | 2014-2018 | |
| 32 | Mark Dudley# | 10 | 2013-2016 | |
| 32 | Randy Fischer# | 10 | 2020-2021 | |
| 32 | Ernie Hancock | 10 | 2012-2016 | |
| 32 | Jason Henley# | 10 | 2015-2019 | |
| 32 | Tim Killeen# | 10 | 2014-2018 | |
| 32 | Joaquin Lira# | 10 | 2016-2019 | |
| 32 | Vinny Luna# | 10 | 2014-2016 | |
| 32 | Luis Najera# | 10 | 2019-2019 | |
| 32 | Jose Navarro | 10 | 2012-2014 | |
| 32 | Chris Phillips# | 10 | 2018-2021 | |
| 32 | Jalen Priestley | 10 | 2012-2015 | |
| 32 | Frank Sarabia# | 10 | 2012-2015 | |
| 32 | Jeff Sharp# | 10 | 2018-2020 | |
| 32 | J.D. Vernon# | 10 | 2012-2015 | |
| 50 | Gary Barone# | 9 | 2012-2013 | |
| 50 | John Bickel# | 9 | 2019-2021 | |
| 50 | Fernando Colin | 9 | 2014-2019 | |
| 50 | Mike Criswell# | 9 | 2015-2017 | |
| 50 | Kevin Daniels# | 9 | 2015-2018 | |
| 50 | Chris Foore# | 9 | 2012-2015 | |
| 50 | Joe Hart# | 9 | 2012-2013 | |
| 50 | Matt Haselden# | 9 | 2018-2021 | |
| 50 | Ricky Hill | 9 | 2012-2018 | |
| 50 | Ed Jenkins# | 9 | 2012-2015 | |
| 50 | Beau Larson# | 9 | 2019-2020 | |
| 50 | Luis Lozano | 9 | 2012-2015 | |
| 50 | Rusty McCall | 9 | 2013-2017 | |
| 50 | Matt McCracken# | 9 | 2018-2021 | |
| 50 | Ryan Parker | 9 | 2012-2015 | |
| 50 | David Pruner# | 9 | 2012-2014 | |
| 50 | Roberto Salazar# | 9 | 2012-2013 | |
| 50 | Tom Schneider | 9 | 2017-2018 | |
| 50 | Jesse Vecchio# | 9 | 2013-2015 | |
| 69 | Robby Alexander | 8 | 2012-2014 | |
| 69 | Nate Benson# | 8 | 2019-2021 | |
| 69 | Adam Bowman# | 8 | 2012-2016 | |
| 69 | Mal Burkes# | 8 | 2020-2021 | |
| 69 | Vic Chou | 8 | 2015-2018 | |
| 69 | Aaron Daniels# | 8 | 2016-2019 | |
| 69 | Nick Douglass# | 8 | 2019-2021 | |
| 69 | David Edgemon# | 8 | 2019-2020 | |
| 69 | Cesar Escobedo# | 8 | 2014-2015 | |
| 69 | Sam Godsey# | 8 | 2013-2016 | |
| 69 | Brent Gudim# | 8 | 2019-2020 | |
| 69 | Adam Haire | 8 | 2014-2016 | |
| 69 | Chris Jacoby# | 8 | 2012-2015 | |
| 69 | Phil Junell# | 8 | 2013-2015 | |
| 69 | Kevin Kovach# | 8 | 2018-2021 | |
| 69 | Dionísio Manteigueiro# | 8 | 2015-2019 | |
| 69 | Ryan Marion | 8 | 2012-2015 | |
| 69 | Gary McIntire | 8 | 2016-2018 | |
| 69 | Paul Mitchell# | 8 | 2020-2021 | |
| 69 | Casey Odom# | 8 | 2017-2021 | |
| 69 | Elias Pena | 8 | 2012-2012 | |
| 69 | Jason Phillips# | 8 | 2017-2018 | |
| 69 | Roberto Reyes | 8 | 2013-2015 | |
| 69 | Eugene Ricci# | 8 | 2019-2021 | |
| 69 | Eddie Saldana | 8 | 2012-2013 | |
| 69 | Simon Scales# | 8 | 2016-2019 | |
| 69 | Josh Shropshire# | 8 | 2016-2017 | |
| 69 | Byron Stanton# | 8 | 2019-2020 | |
| 69 | Will Stone | 8 | 2012-2014 | |
| 69 | Carlos Tellez# | 8 | 2016-2020 | |
| 69 | Jeff Trennepohl | 8 | 2014-2016 | |
| 100 | Nate Ashley# | 7 | 2015-2019 |
