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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# | 29 | 2019-2025 | |
| 6 | Franklin Morales | 28 | 2014-2015 | |
| 6 | Jackson Tetreault# | 28 | 2019-2024 | |
| 8 | Paolo Espino# | 27 | 2013-2024 | |
| 9 | Rico Garcia# | 26 | 2018-2025 | |
| 9 | Matt Heidenreich | 26 | 2014-2017 | |
| 11 | Spencer Adams | 25 | 2017-2019 | |
| 11 | Raul Alcantara# | 25 | 2018-2021 | |
| 11 | Dylan Baker | 25 | 2015-2023 | |
| 11 | Bobby Doran | 25 | 2013-2016 | |
| 11 | Matt Gage# | 25 | 2017-2024 | |
| 16 | Zachary Lovvorn | 24 | 2019-2021 | |
| 17 | Jeremy Beasley# | 23 | 2020-2024 | |
| 17 | Jose Berrios# | 23 | 2014-2017 | |
| 17 | Luis A. Medina# | 23 | 2022-2024 | |
| 20 | Zach Petrick | 22 | 2014-2016 | |
| 20 | Robert Rasmussen | 22 | 2014-2018 | |
| 20 | Armando Rodriguez | 22 | 2013-2016 | |
| 23 | Kyle Heckathorn | 21 | 2013-2016 | |
| 23 | Gerardo Reyes# | 21 | 2020-2022 | |
| 25 | David Hess | 20 | 2015-2021 | |
| 25 | Kanekoa Texeira | 20 | 2013-2016 | |
| 25 | Alex Wimmers | 20 | 2013-2018 | |
| 28 | D.L. Hall# | 19 | 2020-2022 | |
| 28 | Thomas Lee | 19 | 2019-2022 | |
| 28 | Jose Mesa Jr. | 19 | 2018-2023 | |
| 28 | Andrew Painter# | 19 | 2023-2024 | |
| 28 | Stephen Shackleford | 19 | 2013-2017 | |
| 28 | Joshua Smith | 19 | 2015-2020 | |
| 28 | Jerry Sullivan | 19 | 2013-2020 | |
| 28 | Jake Thompson | 19 | 2014-2015 | |
| 36 | Andrew Albers | 18 | 2013-2015 | |
| 36 | Marc Brakeman | 18 | 2018-2021 | |
| 36 | Josh Degraaf | 18 | 2019-2021 | |
| 36 | Bryan Evans | 18 | 2013-2016 | |
| 36 | Mike Franco | 18 | 2018-2021 | |
| 36 | Ryan Jensen# | 18 | 2022-2024 | |
| 36 | Dillon McNamara | 18 | 2018-2021 | |
| 36 | Martin Perez# | 18 | 2013-2019 | |
| 36 | Tyler Phillips# | 18 | 2021-2024 | |
| 36 | Jason Stoffel | 18 | 2013-2017 | |
| 36 | Allen Webster | 18 | 2013-2020 | |
| 36 | Scott Williams | 18 | 2018-2021 | |
| 48 | Chad Bell | 17 | 2014-2017 | |
| 48 | Johnny Fasola | 17 | 2017-2021 | |
| 48 | Austin Gomber# | 17 | 2017-2018 | |
| 48 | Rob Kaminsky | 17 | 2016-2019 | |
| 48 | Greg Nappo | 17 | 2016-2018 | |
| 48 | Nick Rumbelow | 17 | 2017-2024 | |
| 54 | Aaron Brooks# | 16 | 2014-2024 | |
| 54 | Trevor Clifton# | 16 | 2020-2024 | |
| 54 | Ross Detwiler | 16 | 2016-2019 | |
| 54 | Kyle Hart# | 16 | 2019-2023 | |
| 54 | Tyler Higgins | 16 | 2019-2021 | |
| 54 | Stephen Kohlscheen | 16 | 2015-2017 | |
| 54 | Damien Magnifico | 16 | 2017-2020 | |
| 54 | Stephen Nogosek# | 16 | 2018-2022 | |
| 54 | Reese Olson# | 16 | 2022-2023 | |
| 54 | Dalton Sawyer | 16 | 2018-2022 | |
| 54 | Bo Schultz | 16 | 2014-2017 | |
| 54 | Chase Silseth# | 16 | 2023-2024 | |
| 54 | Jess Todd | 16 | 2013-2016 | |
| 67 | Daniel Corcino | 15 | 2013-2017 | |
| 67 | Kyle Dowdy | 15 | 2016-2021 | |
| 67 | Daniel Espino# | 15 | 2021-2023 | |
| 67 | Ashton Goudeau | 15 | 2017-2022 | |
| 67 | Matt Hoffman | 15 | 2013-2015 | |
| 67 | Ben Holmes | 15 | 2019-2023 | |
| 67 | Chih-Wei Hu | 15 | 2019-2023 | |
| 67 | A.J. Morris | 15 | 2013-2017 | |
| 67 | Zachary Neal | 15 | 2015-2017 | |
| 67 | Todd Redmond | 15 | 2017-2019 | |
| 67 | Josh Rogers# | 15 | 2019-2023 | |
| 67 | Daniel Slania | 15 | 2017-2021 | |
| 67 | Pedro Vasquez | 15 | 2019-2022 | |
| 67 | Ryan Weathers# | 15 | 2022-2024 | |
| 81 | Mick Abel# | 14 | 2023-2024 | |
| 81 | Buddy Baumann | 14 | 2013-2016 | |
| 81 | Jose De Paula | 14 | 2013-2014 | |
| 81 | Gordon Graceffo# | 14 | 2023-2025 | |
| 81 | Carlos Hernandez | 14 | 2014-2018 | |
| 81 | Travis Lakins# | 14 | 2017-2023 | |
| 81 | Kyle Lotzkar | 14 | 2013-2014 | |
| 81 | Griff McGarry# | 14 | 2023-2024 | |
| 81 | Benton Moss | 14 | 2016-2020 | |
| 81 | Chris Murphy# | 14 | 2023-2024 | |
| 81 | Joey Murray# | 14 | 2020-2024 | |
| 81 | Colin Peluse# | 14 | 2022-2024 | |
| 81 | Chad Rogers | 14 | 2014-2015 | |
| 81 | John Schreiber# | 14 | 2017-2022 | |
| 81 | Kevin Shackelford | 14 | 2016-2018 | |
| 81 | David Speer | 14 | 2019-2021 | |
| 97 | Jon Edwards | 13 | 2015-2021 | |
| 97 | Nick Gardewine | 13 | 2018-2023 | |
| 97 | Reed Garrett# | 13 | 2017-2023 | |
| 97 | Angel Heredia | 13 | 2018-2019 |
