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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Eric Hacker | 49 | 2017-2022 | |
| 2 | Christopher Beck# | 39 | 2014-2023 | |
| 3 | William Cuevas# | 35 | 2016-2021 | |
| 4 | Logan Darnell# | 32 | 2013-2023 | |
| 4 | Mark Leiter Jr.# | 32 | 2015-2021 | |
| 6 | Tyler Rogers# | 30 | 2015-2017 | |
| 7 | Branden Kline | 28 | 2014-2016 | |
| 8 | Conor Harber# | 26 | 2016-2021 | |
| 9 | Domingo Acevedo# | 25 | 2016-2018 | |
| 9 | Joely Rodriguez# | 25 | 2015-2020 | |
| 11 | Kyle Cody# | 24 | 2018-2020 | |
| 11 | Patrick Francescon | 24 | 2013-2015 | |
| 11 | Jacob Lee | 24 | 2014-2016 | |
| 14 | John Cornely | 22 | 2013-2017 | |
| 14 | Jimmy Gillheeney | 22 | 2013-2015 | |
| 14 | Jay Jackson# | 22 | 2013-2021 | |
| 14 | James Marvel# | 22 | 2021-2023 | |
| 14 | Travis Radke | 22 | 2016-2019 | |
| 19 | Justin Ferrell | 21 | 2018-2019 | |
| 19 | Pierce Johnson# | 21 | 2014-2015 | |
| 19 | Ryan O'Rourke | 21 | 2014-2022 | |
| 19 | Franklin Perez# | 21 | 2016-2020 | |
| 19 | Tyler Phillips# | 21 | 2019-2020 | |
| 19 | Tyler Pill | 21 | 2014-2019 | |
| 19 | Tayler Scott | 21 | 2016-2019 | |
| 19 | Tanner Tully# | 21 | 2018-2021 | |
| 27 | Casey Bloomquist | 20 | 2018-2023 | |
| 27 | Luis Diaz | 20 | 2015-2017 | |
| 27 | Bernardo Flores# | 20 | 2017-2020 | |
| 27 | Dylan Floro# | 20 | 2014-2016 | |
| 27 | Matt Purke | 20 | 2014-2017 | |
| 27 | Adonis Uceta# | 20 | 2018-2023 | |
| 33 | P.J. Conlon# | 19 | 2017-2023 | |
| 33 | Jake Jewell# | 19 | 2017-2023 | |
| 33 | Raudel Lazo | 19 | 2014-2017 | |
| 33 | Chris Mathewson# | 19 | 2019-2022 | |
| 33 | Zachary Nuding | 19 | 2014-2016 | |
| 33 | Brady Puckett# | 19 | 2019-2023 | |
| 33 | Cory Taylor | 19 | 2017-2020 | |
| 33 | Zack Trageton# | 19 | 2020-2023 | |
| 41 | Frank Duncan# | 18 | 2017-2021 | |
| 41 | Tyler Glasnow# | 18 | 2014-2015 | |
| 41 | David Hill# | 18 | 2017-2019 | |
| 41 | Christopher Kirsch | 18 | 2016-2017 | |
| 41 | Marcelo Martinez# | 18 | 2020-2021 | |
| 41 | Luis Mateo | 18 | 2014-2017 | |
| 41 | Jared Robinson# | 18 | 2016-2023 | |
| 41 | Matthew Tracy | 18 | 2013-2014 | |
| 41 | Julio Urias# | 18 | 2015-2016 | |
| 50 | Brock Dykxhoorn | 17 | 2017-2023 | |
| 50 | Chris Jensen | 17 | 2016-2018 | |
| 50 | Bud Jeter | 17 | 2015-2020 | |
| 50 | Tyler Mark# | 17 | 2019-2023 | |
| 50 | Gennison Reyes | 17 | 2015-2018 | |
| 50 | Austin Ross | 17 | 2013-2014 | |
| 50 | Jose Urena# | 17 | 2013-2019 | |
| 57 | Brady Aiken | 16 | 2018-2019 | |
| 57 | Matt Allan# | 16 | 2021-2023 | |
| 57 | D.J. Baxendale | 16 | 2016-2017 | |
| 57 | Beau Burrows# | 16 | 2018-2020 | |
| 57 | Jordan Guerrero# | 16 | 2017-2023 | |
| 57 | Ryan Lillie# | 16 | 2020-2021 | |
| 57 | Brett McKinney | 16 | 2016-2017 | |
| 57 | James Reeves | 16 | 2019-2023 | |
| 57 | Kraig Sitton | 16 | 2015-2017 | |
| 57 | Giovanni Soto | 16 | 2013-2014 | |
| 67 | Trevor Clifton# | 15 | 2018-2019 | |
| 67 | Tyler Eppler# | 15 | 2019-2023 | |
| 67 | Brett Graves | 15 | 2017-2021 | |
| 67 | Connor Johnstone# | 15 | 2019-2021 | |
| 67 | Andrew Jordan# | 15 | 2016-2023 | |
| 67 | Rainy Lara | 15 | 2014-2017 | |
| 67 | Reid Love | 15 | 2018-2023 | |
| 67 | Joshua Lucas# | 15 | 2017-2023 | |
| 67 | Kevin McGowan | 15 | 2018-2020 | |
| 67 | Trevor Megill# | 15 | 2019-2021 | |
| 67 | Dane Myers# | 15 | 2021-2023 | |
| 67 | Justin Nicolino | 15 | 2014-2014 | |
| 67 | Henry Owens | 15 | 2013-2014 | |
| 67 | Emilio Pagan# | 15 | 2016-2018 | |
| 67 | Yacksel Rios# | 15 | 2021-2023 | |
| 67 | Colin Rodgers# | 15 | 2015-2017 | |
| 67 | Mitch Stallings# | 15 | 2020-2023 | |
| 67 | Corey Taylor# | 15 | 2016-2017 | |
| 67 | Drew Verhagen# | 15 | 2020-2021 | |
| 67 | Cody Wheeler | 15 | 2013-2015 | |
| 87 | Brett Adcock# | 14 | 2018-2021 | |
| 87 | Blake Bass# | 14 | 2016-2022 | |
| 87 | Jonathan Bowlan# | 14 | 2020-2021 | |
| 87 | Ryan Carpenter# | 14 | 2013-2016 | |
| 87 | Gerardo Carrillo# | 14 | 2022-2022 | |
| 87 | Tucker Davidson# | 14 | 2018-2019 | |
| 87 | Dean Deetz# | 14 | 2018-2020 | |
| 87 | Jonathan Dziedzic | 14 | 2017-2020 | |
| 87 | Percy Garner | 14 | 2013-2019 | |
| 87 | Jordan M. Guerrero# | 14 | 2018-2022 | |
| 87 | Blake Logan | 14 | 2013-2014 | |
| 87 | Jake Lyons# | 14 | 2020-2023 | |
| 87 | Christopher Manno | 14 | 2013-2015 | |
| 87 | Roman Mendez# | 14 | 2013-2020 |
