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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 | |
| 3 | William McKernan# | 10 | 2015-2016 | |
| 6 | Corey Baker# | 9 | 2016-2017 | |
| 6 | Pat Burkholder# | 9 | 2018-2019 | |
| 6 | Tim Driskill# | 9 | 2016-2017 | |
| 6 | Greg Mortenson# | 9 | 2017-2018 | |
| 6 | Matt Reilly# | 9 | 2017-2018 | |
| 6 | Jeff Weingart# | 9 | 2017-2018 | |
| 12 | Amari Allard# | 8 | 2017-2018 | |
| 12 | Justin Buchan# | 8 | 2015-2016 | |
| 12 | Joe Cohen# | 8 | 2018-2019 | |
| 12 | Kennedy Heath# | 8 | 2017-2018 | |
| 12 | Colby Heim# | 8 | 2018-2019 | |
| 12 | Josh Herman# | 8 | 2013-2014 | |
| 12 | Jesse Morales# | 8 | 2018-2019 | |
| 12 | Jose Nunez# | 8 | 2018-2019 | |
| 12 | Steve Turner# | 8 | 2015-2016 | |
| 21 | Myles Blondin | 7 | 2013-2014 | |
| 21 | Vinny Ceja# | 7 | 2018-2018 | |
| 21 | Tim Cook# | 7 | 2016-2017 | |
| 21 | Josh Cranford# | 7 | 2016-2017 | |
| 21 | Miguel del Real# | 7 | 2018-2019 | |
| 21 | Nick Dragon# | 7 | 2015-2015 | |
| 21 | Ryan Dripps# | 7 | 2015-2016 | |
| 21 | Ernie Fields# | 7 | 2019-2020 | |
| 21 | John Finberg# | 7 | 2016-2017 | |
| 21 | Ben Krueger# | 7 | 2021-2021 | |
| 21 | Rich Lashley# | 7 | 2017-2018 | |
| 21 | Chris Mahaney# | 7 | 2016-2017 | |
| 21 | Wayne Marcks# | 7 | 2014-2015 | |
| 21 | Josh Pegan# | 7 | 2019-2020 | |
| 21 | Nick Pelkey# | 7 | 2013-2014 | |
| 21 | Dakota Penwell# | 7 | 2017-2018 | |
| 21 | Bob Rowe# | 7 | 2019-2020 | |
| 21 | Edwards Sandoval# | 7 | 2015-2015 | |
| 21 | Eddie Sarabia# | 7 | 2020-2020 | |
| 21 | Bill Schuman# | 7 | 2019-2020 | |
| 21 | Marcus Scott# | 7 | 2018-2019 | |
| 21 | Andrew Severson# | 7 | 2014-2014 | |
| 21 | Josh Shane# | 7 | 2015-2016 | |
| 21 | Ken Van Gundy# | 7 | 2020-2021 | |
| 21 | Jayden Vinston# | 7 | 2018-2019 | |
| 21 | Jayden Williams# | 7 | 2018-2019 | |
| 21 | J.J. Wilson# | 7 | 2015-2016 | |
| 21 | Chris Yarbrough# | 7 | 2018-2019 | |
| 49 | Andres Aguilera# | 6 | 2012-2012 | |
| 49 | Geoff Barnwell# | 6 | 2019-2020 | |
| 49 | Eric Baysinger# | 6 | 2015-2016 | |
| 49 | Jody Benincasa# | 6 | 2020-2020 | |
| 49 | Chris Benson# | 6 | 2015-2015 | |
| 49 | Miguel Berrios# | 6 | 2016-2016 | |
| 49 | Adam Bowman# | 6 | 2016-2017 | |
| 49 | Jeff Bozman | 6 | 2012-2013 | |
| 49 | Brian Breen# | 6 | 2013-2013 | |
| 49 | Travis Brown# | 6 | 2013-2014 | |
| 49 | Jose Carbajal# | 6 | 2018-2019 | |
| 49 | Juan Carrillo# | 6 | 2016-2017 | |
| 49 | Tim Covert# | 6 | 2015-2016 | |
| 49 | Kevin Daniels# | 6 | 2015-2015 | |
| 49 | Jamel DeLaine# | 6 | 2019-2020 | |
| 49 | Joe Dixon# | 6 | 2016-2017 | |
| 49 | Seth Ells | 6 | 2013-2014 | |
| 49 | Dustin Engstrom# | 6 | 2019-2020 | |
| 49 | John Froerer# | 6 | 2013-2013 | |
| 49 | Kenny Fuzzell# | 6 | 2013-2013 | |
| 49 | Guillermo Gonzalez# | 6 | 2019-2020 | |
| 49 | Phil Goodman | 6 | 2012-2012 | |
| 49 | Dave Greer# | 6 | 2019-2020 | |
| 49 | Jonathan Harvey# | 6 | 2016-2016 | |
| 49 | Jordan Hawkins# | 6 | 2015-2016 | |
| 49 | Mike Hietala# | 6 | 2017-2018 | |
| 49 | Shane Hubbard# | 6 | 2012-2012 | |
| 49 | John Huff# | 6 | 2012-2013 | |
| 49 | Brian Hughes# | 6 | 2019-2020 | |
| 49 | Stephen Kolsrud | 6 | 2015-2016 | |
| 49 | Alan Kramer | 6 | 2012-2013 | |
| 49 | Tommy LaBiche# | 6 | 2017-2018 | |
| 49 | Beau Larson# | 6 | 2018-2018 | |
| 49 | Rick Lee# | 6 | 2013-2014 | |
| 49 | Tim Lemar# | 6 | 2019-2020 | |
| 49 | Tim Little# | 6 | 2013-2014 | |
| 49 | Michael Lowery# | 6 | 2014-2015 | |
| 49 | Dave Luca# | 6 | 2016-2017 | |
| 49 | Steve Lund# | 6 | 2016-2017 | |
| 49 | Mike Marlow# | 6 | 2018-2018 | |
| 49 | Chris Marquis# | 6 | 2015-2015 | |
| 49 | Graham Mercer# | 6 | 2018-2019 | |
| 49 | Dan Miller# | 6 | 2013-2014 | |
| 49 | Shane Mittlesteadt | 6 | 2012-2013 | |
| 49 | Mark Moore# | 6 | 2012-2012 | |
| 49 | Ian Muenkel# | 6 | 2018-2019 | |
| 49 | Brian Norfolk# | 6 | 2017-2018 | |
| 49 | Arnold Novak# | 6 | 2015-2016 | |
| 49 | Bobby Nowlin# | 6 | 2020-2020 | |
| 49 | Marc O'Brian# | 6 | 2016-2017 | |
| 49 | Mason Owenby# | 6 | 2015-2016 | |
| 49 | Nick Palazzo# | 6 | 2017-2018 |
