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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 | Greg Mortenson# | 9 | 2017-2018 | |
| 5 | Matt Reilly# | 9 | 2017-2018 | |
| 5 | Jeff Weingart# | 9 | 2017-2018 | |
| 11 | Amari Allard# | 8 | 2017-2018 | |
| 11 | Justin Buchan# | 8 | 2015-2016 | |
| 11 | Joe Cohen# | 8 | 2018-2019 | |
| 11 | Kennedy Heath# | 8 | 2017-2018 | |
| 11 | Colby Heim# | 8 | 2018-2019 | |
| 11 | Josh Herman | 8 | 2013-2014 | |
| 11 | Ben Krueger# | 8 | 2021-2021 | |
| 11 | Jesse Morales# | 8 | 2018-2019 | |
| 11 | Jose Nunez# | 8 | 2018-2019 | |
| 20 | Myles Blondin | 7 | 2013-2014 | |
| 20 | Vinny Ceja# | 7 | 2018-2018 | |
| 20 | Tim Cook | 7 | 2016-2017 | |
| 20 | Josh Cranford# | 7 | 2016-2017 | |
| 20 | Miguel del Real# | 7 | 2018-2019 | |
| 20 | Nick Dragon# | 7 | 2015-2015 | |
| 20 | Ernie Fields# | 7 | 2019-2020 | |
| 20 | John Finberg# | 7 | 2016-2017 | |
| 20 | Rich Lashley# | 7 | 2017-2018 | |
| 20 | Franklin Lugo# | 7 | 2021-2022 | |
| 20 | Chris Mahaney# | 7 | 2016-2017 | |
| 20 | Wayne Marcks | 7 | 2014-2015 | |
| 20 | Mike Martinez# | 7 | 2021-2022 | |
| 20 | Josh Pegan# | 7 | 2019-2020 | |
| 20 | Nick Pelkey | 7 | 2013-2014 | |
| 20 | Dakota Penwell# | 7 | 2017-2018 | |
| 20 | Edwards Sandoval# | 7 | 2015-2015 | |
| 20 | Eddie Sarabia# | 7 | 2020-2020 | |
| 20 | Bill Schuman# | 7 | 2019-2020 | |
| 20 | Marcus Scott# | 7 | 2018-2019 | |
| 20 | Andrew Severson | 7 | 2014-2014 | |
| 20 | Josh Shane# | 7 | 2015-2016 | |
| 20 | Jayden Vinston# | 7 | 2018-2019 | |
| 20 | Jayden Williams# | 7 | 2018-2019 | |
| 20 | Chris Yarbrough# | 7 | 2018-2019 | |
| 45 | Andres Aguilera | 6 | 2012-2012 | |
| 45 | Jody Benincasa# | 6 | 2020-2020 | |
| 45 | Chris Benson# | 6 | 2015-2015 | |
| 45 | Miguel Berrios# | 6 | 2016-2016 | |
| 45 | Adam Bowman# | 6 | 2016-2017 | |
| 45 | Jeff Bozman | 6 | 2012-2013 | |
| 45 | Brian Breen# | 6 | 2013-2013 | |
| 45 | Travis Brown | 6 | 2013-2014 | |
| 45 | Jose Carbajal# | 6 | 2018-2019 | |
| 45 | Juan Carrillo# | 6 | 2016-2017 | |
| 45 | Tim Covert# | 6 | 2015-2016 | |
| 45 | Kevin Daniels# | 6 | 2015-2015 | |
| 45 | Jamel DeLaine# | 6 | 2019-2020 | |
| 45 | Joe Dixon# | 6 | 2016-2017 | |
| 45 | Joel Edmondson# | 6 | 2020-2021 | |
| 45 | Seth Ells | 6 | 2013-2014 | |
| 45 | Dustin Engstrom# | 6 | 2019-2020 | |
| 45 | Morgan Felty# | 6 | 2021-2022 | |
| 45 | John Froerer# | 6 | 2013-2013 | |
| 45 | Kenny Fuzzell# | 6 | 2013-2013 | |
| 45 | Guillermo Gonzalez# | 6 | 2019-2020 | |
| 45 | Phil Goodman | 6 | 2012-2012 | |
| 45 | Jonathan Harvey# | 6 | 2016-2016 | |
| 45 | Jordan Hawkins# | 6 | 2015-2016 | |
| 45 | Mike Hietala# | 6 | 2017-2018 | |
| 45 | Shane Hubbard | 6 | 2012-2012 | |
| 45 | John Huff | 6 | 2012-2013 | |
| 45 | Brian Hughes# | 6 | 2019-2020 | |
| 45 | Stephen Kolsrud | 6 | 2015-2016 | |
| 45 | Alan Kramer | 6 | 2012-2013 | |
| 45 | Tommy LaBiche# | 6 | 2017-2018 | |
| 45 | Beau Larson# | 6 | 2018-2018 | |
| 45 | Rick Lee | 6 | 2013-2014 | |
| 45 | Tim Lemar# | 6 | 2019-2020 | |
| 45 | Tim Little | 6 | 2013-2014 | |
| 45 | Dave Luca# | 6 | 2016-2017 | |
| 45 | Steve Lund# | 6 | 2016-2017 | |
| 45 | Mike Marlow | 6 | 2018-2018 | |
| 45 | Chris Marquis# | 6 | 2015-2015 | |
| 45 | Graham Mercer# | 6 | 2018-2019 | |
| 45 | Dan Miller# | 6 | 2013-2014 | |
| 45 | Shane Mittlesteadt | 6 | 2012-2013 | |
| 45 | Mark Moore# | 6 | 2012-2012 | |
| 45 | Ian Muenkel# | 6 | 2018-2019 | |
| 45 | Brian Norfolk# | 6 | 2017-2018 | |
| 45 | Arnold Novak# | 6 | 2015-2016 | |
| 45 | Bobby Nowlin# | 6 | 2020-2020 | |
| 45 | Marc O'Brian# | 6 | 2016-2017 | |
| 45 | Nick Palazzo# | 6 | 2017-2018 | |
| 45 | Ken Pavlich# | 6 | 2016-2017 | |
| 45 | Ryan Perkins# | 6 | 2018-2019 | |
| 45 | Armando Ramirez# | 6 | 2012-2013 | |
| 45 | Dustin Richards# | 6 | 2020-2021 | |
| 45 | David Rivas# | 6 | 2018-2019 | |
| 45 | Sean Roberts | 6 | 2012-2013 | |
| 45 | Marco Rodriguez | 6 | 2015-2016 |
