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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 | Tim Driskill | 9 | 2016-2017 | |
| 5 | Mike Martinez# | 9 | 2021-2022 | |
| 5 | Greg Mortenson | 9 | 2017-2018 | |
| 5 | Tom Thomsen# | 9 | 2024-2025 | |
| 5 | Zachary Vanderlip# | 9 | 2024-2025 | |
| 5 | Jeff Weingart# | 9 | 2017-2018 | |
| 12 | Amari Allard# | 8 | 2017-2018 | |
| 12 | Bryan Andriano# | 8 | 2023-2024 | |
| 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 | Jose Nunez# | 8 | 2018-2019 | |
| 12 | Chris Scott# | 8 | 2024-2025 | |
| 23 | Alpha Bauman# | 7 | 2023-2024 | |
| 23 | Myles Blondin | 7 | 2013-2014 | |
| 23 | Vinny Ceja# | 7 | 2018-2018 | |
| 23 | Tim Cook | 7 | 2016-2017 | |
| 23 | Nick Dragon# | 7 | 2015-2015 | |
| 23 | Ernie Fields# | 7 | 2019-2020 | |
| 23 | Rich Lashley | 7 | 2017-2018 | |
| 23 | Wayne Marcks | 7 | 2014-2015 | |
| 23 | Phil McIntosh# | 7 | 2025-2025 | |
| 23 | Josh Pegan# | 7 | 2019-2020 | |
| 23 | Nick Pelkey | 7 | 2013-2014 | |
| 23 | Dakota Penwell | 7 | 2017-2018 | |
| 23 | Edwards Sandoval | 7 | 2015-2015 | |
| 23 | Eddie Sarabia# | 7 | 2020-2020 | |
| 23 | Marcus Scott | 7 | 2018-2019 | |
| 23 | Andrew Severson | 7 | 2014-2014 | |
| 23 | Pat Tanner# | 7 | 2025-2025 | |
| 23 | Jayden Williams | 7 | 2018-2019 | |
| 23 | 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 | Juan Carrillo | 6 | 2016-2017 | |
| 42 | Oscar Coronado# | 6 | 2023-2024 | |
| 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 | 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 | Seth Johnson# | 6 | 2023-2024 | |
| 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 Little | 6 | 2013-2014 | |
| 42 | Mike Marlow | 6 | 2018-2018 | |
| 42 | Chris Marquis# | 6 | 2015-2015 | |
| 42 | Alex Martinez# | 6 | 2024-2025 | |
| 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 | Ken Pavlich | 6 | 2016-2017 | |
| 42 | Ryan Perkins | 6 | 2018-2019 | |
| 42 | Armando Ramirez# | 6 | 2012-2013 | |
| 42 | Dustin Richards# | 6 | 2020-2021 | |
| 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 | Corey Shanahan# | 6 | 2024-2025 | |
| 42 | Bob Tober | 6 | 2014-2014 | |
| 42 | Preston Todd | 6 | 2013-2013 | |
| 42 | Nick Touchet | 6 | 2013-2013 | |
| 42 | Frank Tressler | 6 | 2019-2020 | |
| 42 | Ray Vernier# | 6 | 2020-2021 |
