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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Ricky Alvarez# | 12 | 2015-2016 | |
| 2 | Donnie Marcus# | 11 | 2013-2014 | |
| 3 | Bobby Hilliker | 10 | 2013-2014 | |
| 3 | Charlie Hunter# | 10 | 2019-2020 | |
| 5 | Corey Baker# | 9 | 2016-2017 | |
| 5 | Pat Burkholder# | 9 | 2018-2019 | |
| 5 | Tim Driskill# | 9 | 2016-2017 | |
| 5 | Mike Martinez# | 9 | 2021-2022 | |
| 5 | Greg Mortenson# | 9 | 2017-2018 | |
| 5 | Matt Reilly# | 9 | 2017-2018 | |
| 5 | Jeff Weingart# | 9 | 2017-2018 | |
| 12 | Amari Allard# | 8 | 2017-2018 | |
| 12 | Justin Buchan | 8 | 2015-2016 | |
| 12 | Joe Cohen# | 8 | 2018-2019 | |
| 12 | Mike Hammond# | 8 | 2022-2022 | |
| 12 | Kennedy Heath# | 8 | 2017-2018 | |
| 12 | Colby Heim# | 8 | 2018-2019 | |
| 12 | Josh Herman | 8 | 2013-2014 | |
| 12 | Ben Krueger# | 8 | 2021-2021 | |
| 12 | Jesse Morales# | 8 | 2018-2019 | |
| 12 | Jose Nunez# | 8 | 2018-2019 | |
| 22 | Myles Blondin | 7 | 2013-2014 | |
| 22 | Vinny Ceja# | 7 | 2018-2018 | |
| 22 | Tim Cook | 7 | 2016-2017 | |
| 22 | Miguel del Real# | 7 | 2018-2019 | |
| 22 | Nick Dragon# | 7 | 2015-2015 | |
| 22 | Ernie Fields# | 7 | 2019-2020 | |
| 22 | Shane Hill# | 7 | 2023-2023 | |
| 22 | Rich Lashley# | 7 | 2017-2018 | |
| 22 | Wayne Marcks | 7 | 2014-2015 | |
| 22 | Josh Pegan# | 7 | 2019-2020 | |
| 22 | Nick Pelkey | 7 | 2013-2014 | |
| 22 | Dakota Penwell# | 7 | 2017-2018 | |
| 22 | Edwards Sandoval# | 7 | 2015-2015 | |
| 22 | Eddie Sarabia# | 7 | 2020-2020 | |
| 22 | Bill Schuman# | 7 | 2019-2020 | |
| 22 | Marcus Scott# | 7 | 2018-2019 | |
| 22 | Andrew Severson | 7 | 2014-2014 | |
| 22 | Jayden Vinston# | 7 | 2018-2019 | |
| 22 | Jayden Williams# | 7 | 2018-2019 | |
| 22 | Chris Yarbrough# | 7 | 2018-2019 | |
| 42 | Andres Aguilera | 6 | 2012-2012 | |
| 42 | Jody Benincasa# | 6 | 2020-2020 | |
| 42 | Chris Benson# | 6 | 2015-2015 | |
| 42 | Miguel Berrios# | 6 | 2016-2016 | |
| 42 | Adam Bowman | 6 | 2016-2017 | |
| 42 | Jeff Bozman | 6 | 2012-2013 | |
| 42 | Brian Breen# | 6 | 2013-2013 | |
| 42 | Travis Brown | 6 | 2013-2014 | |
| 42 | Jose Carbajal# | 6 | 2018-2019 | |
| 42 | Juan Carrillo | 6 | 2016-2017 | |
| 42 | Tim Covert | 6 | 2015-2016 | |
| 42 | Kevin Daniels# | 6 | 2015-2015 | |
| 42 | Jamel DeLaine# | 6 | 2019-2020 | |
| 42 | Joe Dixon# | 6 | 2016-2017 | |
| 42 | Joel Edmondson# | 6 | 2020-2021 | |
| 42 | Seth Ells | 6 | 2013-2014 | |
| 42 | Dustin Engstrom# | 6 | 2019-2020 | |
| 42 | Morgan Felty# | 6 | 2021-2022 | |
| 42 | John Froerer# | 6 | 2013-2013 | |
| 42 | Kenny Fuzzell# | 6 | 2013-2013 | |
| 42 | Guillermo Gonzalez# | 6 | 2019-2020 | |
| 42 | Phil Goodman | 6 | 2012-2012 | |
| 42 | Jonathan Harvey# | 6 | 2016-2016 | |
| 42 | Mike Hietala# | 6 | 2017-2018 | |
| 42 | Shane Hubbard | 6 | 2012-2012 | |
| 42 | John Huff | 6 | 2012-2013 | |
| 42 | Brian Hughes# | 6 | 2019-2020 | |
| 42 | Stephen Kolsrud | 6 | 2015-2016 | |
| 42 | Alan Kramer | 6 | 2012-2013 | |
| 42 | Tommy LaBiche# | 6 | 2017-2018 | |
| 42 | Beau Larson# | 6 | 2018-2018 | |
| 42 | Rick Lee | 6 | 2013-2014 | |
| 42 | Tim Lemar# | 6 | 2019-2020 | |
| 42 | Tim Little | 6 | 2013-2014 | |
| 42 | Steve Lund# | 6 | 2016-2017 | |
| 42 | Mike Marlow | 6 | 2018-2018 | |
| 42 | Chris Marquis# | 6 | 2015-2015 | |
| 42 | Graham Mercer# | 6 | 2018-2019 | |
| 42 | Dan Miller# | 6 | 2013-2014 | |
| 42 | Shane Mittlesteadt | 6 | 2012-2013 | |
| 42 | Mark Moore# | 6 | 2012-2012 | |
| 42 | Ian Muenkel# | 6 | 2018-2019 | |
| 42 | Brian Norfolk# | 6 | 2017-2018 | |
| 42 | Arnold Novak# | 6 | 2015-2016 | |
| 42 | Bobby Nowlin# | 6 | 2020-2020 | |
| 42 | Marc O'Brian# | 6 | 2016-2017 | |
| 42 | Nick Palazzo# | 6 | 2017-2018 | |
| 42 | Ken Pavlich | 6 | 2016-2017 | |
| 42 | Ryan Perkins# | 6 | 2018-2019 | |
| 42 | Armando Ramirez# | 6 | 2012-2013 | |
| 42 | Dustin Richards# | 6 | 2020-2021 | |
| 42 | David Rivas# | 6 | 2018-2019 | |
| 42 | Sean Roberts | 6 | 2012-2013 | |
| 42 | Marco Rodriguez | 6 | 2015-2016 | |
| 42 | Jorge Santos# | 6 | 2016-2017 | |
| 42 | Greg Schmit | 6 | 2014-2014 | |
| 42 | Bob Tober | 6 | 2014-2014 | |
| 42 | Preston Todd# | 6 | 2013-2013 | |
| 42 | Nick Touchet | 6 | 2013-2013 |
