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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Billy Bishop# | 65 | 2018-2022 | |
| 2 | Jack Kochanowicz# | 31 | 2020-2023 | |
| 2 | Anthony Roberts# | 31 | 2018-2023 | |
| 4 | Sean Hjelle# | 28 | 2019-2024 | |
| 5 | Ken Waldichuk# | 27 | 2020-2022 | |
| 6 | Curt Allen# | 26 | 2019-2023 | |
| 6 | Nathan Armstrong# | 26 | 2020-2022 | |
| 8 | Alex Early# | 25 | 2022-2023 | |
| 8 | Kyle Rogers# | 25 | 2020-2021 | |
| 10 | T.J. Sikkema# | 23 | 2022-2023 | |
| 11 | Jeff Wiley | 22 | 2016-2018 | |
| 12 | Harry Richardson# | 21 | 2018-2019 | |
| 13 | Jorge Rodríguez# | 20 | 2020-2022 | |
| 13 | Ryan Sims# | 20 | 2020-2022 | |
| 15 | Víctor De La Rosa | 19 | 2014-2015 | |
| 15 | Mason Denaburg# | 19 | 2019-2020 | |
| 15 | Robert LeClair# | 19 | 2019-2023 | |
| 15 | Sixto Sanchez# | 19 | 2020-2020 | |
| 15 | Alvin Tigner# | 19 | 2022-2023 | |
| 15 | Kyle Zimmer | 19 | 2013-2014 | |
| 21 | Alex Meyer | 18 | 2012-2013 | |
| 21 | Alfredo Palma# | 18 | 2019-2021 | |
| 21 | Randol Rojas | 18 | 2012-2015 | |
| 24 | Don Day# | 17 | 2017-2019 | |
| 24 | Jorge Flores# | 17 | 2017-2020 | |
| 24 | Victor Payano# | 17 | 2012-2014 | |
| 24 | Matthew Wisler | 17 | 2015-2016 | |
| 28 | Mick Abel# | 16 | 2022-2023 | |
| 28 | Abel M. De Los Santos# | 16 | 2012-2013 | |
| 28 | Lester Hardy# | 16 | 2020-2024 | |
| 28 | Aaron O'Day# | 16 | 2021-2022 | |
| 32 | Jose Fernandez# | 15 | 2013-2017 | |
| 32 | Juan García# | 15 | 2016-2017 | |
| 32 | Sixto Granados# | 15 | 2021-2023 | |
| 32 | Austin Malinowski# | 15 | 2016-2016 | |
| 32 | Peter Solomon# | 15 | 2018-2020 | |
| 32 | Skylar Spurrier# | 15 | 2021-2021 | |
| 32 | Don Stoneciphe# | 15 | 2020-2022 | |
| 32 | Lawrence Taylor# | 15 | 2015-2017 | |
| 32 | Drew Thurman# | 15 | 2020-2021 | |
| 41 | William Cuevas | 14 | 2014-2014 | |
| 41 | Ty Griffin# | 14 | 2020-2021 | |
| 41 | Dustin Lane# | 14 | 2018-2019 | |
| 41 | Doug Nikhazy# | 14 | 2022-2024 | |
| 41 | George Olsen# | 14 | 2020-2022 | |
| 41 | Carlos Pimentel | 14 | 2012-2013 | |
| 41 | Julio Robina# | 14 | 2023-2023 | |
| 41 | Juan Romero# | 14 | 2014-2014 | |
| 41 | Bobby Simmons# | 14 | 2022-2024 | |
| 41 | Edward Small# | 14 | 2017-2017 | |
| 41 | Michael Torretta# | 14 | 2018-2018 | |
| 41 | Robert Trewen# | 14 | 2018-2021 | |
| 41 | Hayden Wesneski# | 14 | 2019-2022 | |
| 41 | Danny William# | 14 | 2017-2017 | |
| 55 | Rich Beasley# | 13 | 2019-2020 | |
| 55 | Carlos García | 13 | 2014-2015 | |
| 55 | Ken Gary# | 13 | 2018-2018 | |
| 55 | Tony Gutiérrez# | 13 | 2019-2021 | |
| 55 | Ray Harris | 13 | 2014-2014 | |
| 55 | Francisco Muñóz# | 13 | 2019-2022 | |
| 55 | Eduardo Rodriguez# | 13 | 2015-2016 | |
| 55 | Ryan Weathers# | 13 | 2019-2019 | |
| 63 | Brady Aiken# | 12 | 2015-2016 | |
| 63 | Sam Bazley# | 12 | 2020-2021 | |
| 63 | Austin Bergner# | 12 | 2020-2021 | |
| 63 | Tim Cates# | 12 | 2018-2019 | |
| 63 | Robert Gasser# | 12 | 2023-2023 | |
| 63 | José Hernández# | 12 | 2020-2024 | |
| 63 | Will Inman | 12 | 2012-2012 | |
| 63 | Kyle Lofton# | 12 | 2022-2023 | |
| 63 | James Marinan# | 12 | 2022-2022 | |
| 63 | Carlos Martínez# | 12 | 2022-2024 | |
| 63 | José Ortega# | 12 | 2020-2024 | |
| 63 | Griffin Parkinson# | 12 | 2018-2019 | |
| 63 | Albert Peck# | 12 | 2020-2022 | |
| 63 | Juan Ramos# | 12 | 2014-2015 | |
| 63 | Matthew Spalding# | 12 | 2014-2014 | |
| 63 | Calvin Welch# | 12 | 2018-2021 | |
| 79 | Joey Adams# | 11 | 2022-2023 | |
| 79 | Ryan Bollinger | 11 | 2013-2014 | |
| 79 | Taylor Cornelius# | 11 | 2021-2022 | |
| 79 | John Crow# | 11 | 2017-2021 | |
| 79 | J.R. Graham | 11 | 2012-2013 | |
| 79 | Dwight Hanson# | 11 | 2017-2018 | |
| 79 | Hideaki Hirose# | 11 | 2012-2013 | |
| 79 | Tsuramatsu Iguchi# | 11 | 2017-2023 | |
| 79 | Maverick Kingsburry# | 11 | 2022-2022 | |
| 79 | Jacob Meador# | 11 | 2020-2021 | |
| 79 | Riley Pint# | 11 | 2019-2020 | |
| 79 | José Santiago# | 11 | 2017-2017 | |
| 79 | Bob Thomas# | 11 | 2021-2023 | |
| 79 | Blake Witt# | 11 | 2019-2019 | |
| 79 | Ricardo Zapata# | 11 | 2020-2021 | |
| 94 | Noah Cameron# | 10 | 2022-2024 | |
| 94 | Edward Carlson# | 10 | 2020-2020 | |
| 94 | Wes Clark# | 10 | 2019-2019 | |
| 94 | Chase Davis# | 10 | 2022-2022 | |
| 94 | Justin Fall# | 10 | 2021-2023 | |
| 94 | Dave Groves# | 10 | 2015-2016 | |
| 94 | Jon Kent# | 10 | 2017-2018 |
