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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Julian Merryweather# | 39 | 2017-2020 | |
| 1 | Chris Reed | 39 | 2013-2021 | |
| 3 | Eric Jokisch# | 38 | 2014-2018 | |
| 3 | Adam Morgan | 38 | 2013-2023 | |
| 5 | Adonis Medina# | 31 | 2019-2025 | |
| 6 | Paolo Espino# | 29 | 2013-2025 | |
| 6 | Luis A. Medina# | 29 | 2022-2025 | |
| 8 | Franklin Morales | 28 | 2014-2015 | |
| 8 | Jackson Tetreault# | 28 | 2019-2024 | |
| 10 | Jeremy Beasley# | 27 | 2020-2026 | |
| 10 | Rico Garcia# | 27 | 2018-2026 | |
| 10 | Andrew Painter# | 27 | 2023-2025 | |
| 13 | Matt Heidenreich | 26 | 2014-2017 | |
| 14 | Spencer Adams | 25 | 2017-2019 | |
| 14 | Raul Alcantara# | 25 | 2018-2021 | |
| 14 | Dylan Baker | 25 | 2015-2023 | |
| 14 | Bobby Doran | 25 | 2013-2016 | |
| 14 | Matt Gage# | 25 | 2017-2026 | |
| 19 | Zachary Lovvorn | 24 | 2019-2021 | |
| 20 | Mick Abel# | 23 | 2023-2025 | |
| 20 | Jose Berrios# | 23 | 2014-2017 | |
| 22 | Ryan Jensen# | 22 | 2022-2025 | |
| 22 | Zach Petrick | 22 | 2014-2016 | |
| 22 | Robert Rasmussen | 22 | 2014-2018 | |
| 22 | Armando Rodriguez | 22 | 2013-2016 | |
| 26 | Kyle Heckathorn | 21 | 2013-2016 | |
| 26 | Cade Povich# | 21 | 2024-2025 | |
| 26 | Gerardo Reyes# | 21 | 2020-2022 | |
| 29 | David Hess | 20 | 2015-2021 | |
| 29 | Jimmy Joyce# | 20 | 2024-2026 | |
| 29 | Kanekoa Texeira | 20 | 2013-2016 | |
| 29 | Alex Wimmers | 20 | 2013-2018 | |
| 33 | D.L. Hall# | 19 | 2020-2022 | |
| 33 | Thomas Lee | 19 | 2019-2022 | |
| 33 | Jose Mesa Jr. | 19 | 2018-2023 | |
| 33 | Stephen Shackleford | 19 | 2013-2017 | |
| 33 | Joshua Smith | 19 | 2015-2020 | |
| 33 | Jerry Sullivan | 19 | 2013-2020 | |
| 33 | Jake Thompson | 19 | 2014-2015 | |
| 40 | Andrew Albers | 18 | 2013-2015 | |
| 40 | Marc Brakeman | 18 | 2018-2021 | |
| 40 | Josh Degraaf | 18 | 2019-2021 | |
| 40 | Bryan Evans | 18 | 2013-2016 | |
| 40 | Mike Franco | 18 | 2018-2021 | |
| 40 | Dillon McNamara | 18 | 2018-2021 | |
| 40 | Martin Perez# | 18 | 2013-2019 | |
| 40 | Tyler Phillips# | 18 | 2021-2026 | |
| 40 | Alan Rangel# | 18 | 2022-2025 | |
| 40 | Jason Stoffel | 18 | 2013-2017 | |
| 40 | Allen Webster | 18 | 2013-2020 | |
| 40 | Scott Williams | 18 | 2018-2021 | |
| 52 | Chad Bell | 17 | 2014-2017 | |
| 52 | Johnny Fasola | 17 | 2017-2021 | |
| 52 | Austin Gomber# | 17 | 2017-2018 | |
| 52 | Rob Kaminsky | 17 | 2016-2019 | |
| 52 | Greg Nappo | 17 | 2016-2018 | |
| 52 | Nick Rumbelow | 17 | 2017-2024 | |
| 52 | Connor Sadzeck# | 17 | 2017-2025 | |
| 52 | Forrest Whitley# | 17 | 2019-2025 | |
| 60 | Aaron Brooks# | 16 | 2014-2024 | |
| 60 | Trevor Clifton# | 16 | 2020-2024 | |
| 60 | Ross Detwiler | 16 | 2016-2019 | |
| 60 | Kyle Hart# | 16 | 2019-2023 | |
| 60 | Tyler Higgins | 16 | 2019-2021 | |
| 60 | Stephen Kohlscheen | 16 | 2015-2017 | |
| 60 | Luke Leftwich# | 16 | 2020-2025 | |
| 60 | Damien Magnifico | 16 | 2017-2020 | |
| 60 | Stephen Nogosek | 16 | 2018-2022 | |
| 60 | Reese Olson# | 16 | 2022-2023 | |
| 60 | Dalton Sawyer | 16 | 2018-2022 | |
| 60 | Bo Schultz | 16 | 2014-2017 | |
| 60 | Chase Silseth# | 16 | 2023-2024 | |
| 60 | Carson Spiers# | 16 | 2023-2026 | |
| 60 | Jess Todd | 16 | 2013-2016 | |
| 75 | Daniel Corcino | 15 | 2013-2017 | |
| 75 | Garrett Davila# | 15 | 2022-2025 | |
| 75 | Kyle Dowdy | 15 | 2016-2021 | |
| 75 | Daniel Espino# | 15 | 2021-2023 | |
| 75 | Ashton Goudeau | 15 | 2017-2022 | |
| 75 | Matt Hoffman | 15 | 2013-2015 | |
| 75 | Ben Holmes | 15 | 2019-2023 | |
| 75 | Chih-Wei Hu | 15 | 2019-2023 | |
| 75 | Jeff Lindgren# | 15 | 2022-2025 | |
| 75 | A.J. Morris | 15 | 2013-2017 | |
| 75 | Zachary Neal | 15 | 2015-2017 | |
| 75 | Todd Redmond | 15 | 2017-2019 | |
| 75 | Josh Rogers# | 15 | 2019-2023 | |
| 75 | Daniel Slania | 15 | 2017-2021 | |
| 75 | Pedro Vasquez | 15 | 2019-2022 | |
| 75 | Ryan Weathers# | 15 | 2022-2024 | |
| 75 | Jordan Wicks# | 15 | 2023-2025 | |
| 92 | Buddy Baumann | 14 | 2013-2016 | |
| 92 | Jose De Paula | 14 | 2013-2014 | |
| 92 | Gordon Graceffo# | 14 | 2023-2025 | |
| 92 | Carlos Hernandez | 14 | 2014-2018 | |
| 92 | Rhett Kouba# | 14 | 2024-2025 | |
| 92 | Travis Lakins# | 14 | 2017-2023 | |
| 92 | Kyle Lotzkar | 14 | 2013-2014 | |
| 92 | Griff McGarry# | 14 | 2023-2024 | |
| 92 | Benton Moss | 14 | 2016-2020 |
