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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Kendry Flores | 33 | 2015-2018 | |
| 2 | Roberto Padilla | 29 | 2015-2016 | |
| 3 | Júlio Chávez# | 28 | 2018-2020 | |
| 4 | Michael Santana# | 26 | 2014-2020 | |
| 5 | Michael Brown# | 24 | 2015-2018 | |
| 5 | Alexander Carreras | 24 | 2012-2014 | |
| 5 | Tony Leal# | 24 | 2018-2022 | |
| 8 | Ricardo Cortéz | 23 | 2015-2018 | |
| 8 | Raúl Lisboa# | 23 | 2019-2020 | |
| 10 | Matthew Laney | 22 | 2012-2019 | |
| 10 | Matthew Milton# | 22 | 2022-2024 | |
| 10 | Kilby Pena# | 22 | 2016-2020 | |
| 13 | Jonathan Bailey# | 21 | 2016-2020 | |
| 13 | Jacob Beck# | 21 | 2021-2024 | |
| 13 | Christopher Lee# | 21 | 2014-2015 | |
| 16 | Blake Hassebrock | 20 | 2012-2013 | |
| 16 | Adalberto Mejia# | 20 | 2014-2017 | |
| 16 | Marcos Sánchez# | 20 | 2021-2024 | |
| 19 | Craig Bennigson | 19 | 2012-2016 | |
| 19 | Cristia Bishop# | 19 | 2017-2020 | |
| 19 | Rickie Brehaut# | 19 | 2022-2024 | |
| 19 | Isaiah Campbell# | 19 | 2021-2023 | |
| 19 | Kelly Koch# | 19 | 2019-2020 | |
| 19 | Dudley Lewis# | 19 | 2017-2021 | |
| 19 | Gabriel Ynoa# | 19 | 2016-2018 | |
| 26 | Gustavo Gomez | 18 | 2012-2013 | |
| 26 | Jeff Peterson# | 18 | 2021-2023 | |
| 26 | John Williams# | 18 | 2020-2024 | |
| 26 | Michael Ynoa# | 18 | 2014-2017 | |
| 30 | Tyler Brennan# | 17 | 2020-2022 | |
| 30 | John Carter# | 17 | 2020-2023 | |
| 30 | Garrett Gannon# | 17 | 2023-2024 | |
| 30 | Zack Hess# | 17 | 2021-2022 | |
| 30 | Chris Marlowe | 17 | 2012-2014 | |
| 30 | Branden Pinder | 17 | 2016-2017 | |
| 30 | Anthony Richardson# | 17 | 2019-2021 | |
| 30 | Guillermo Rodríguez# | 17 | 2020-2021 | |
| 30 | Taylor Staal# | 17 | 2018-2021 | |
| 30 | Paul Taylor# | 17 | 2019-2022 | |
| 30 | Alejandro Ávila# | 17 | 2018-2023 | |
| 41 | Will Bednar# | 16 | 2023-2023 | |
| 41 | Doug Crawford | 16 | 2019-2020 | |
| 41 | Jon Dixon# | 16 | 2014-2015 | |
| 41 | Ronald Dunham# | 16 | 2017-2017 | |
| 41 | Quirino Forjaz# | 16 | 2021-2024 | |
| 41 | Larry Gamble | 16 | 2016-2022 | |
| 41 | Kevin Gowdy# | 16 | 2021-2021 | |
| 41 | Donald Moody# | 16 | 2020-2023 | |
| 41 | Juan Oramas# | 16 | 2012-2013 | |
| 41 | Ross Seaton | 16 | 2012-2012 | |
| 51 | Mitch Carter# | 15 | 2015-2016 | |
| 51 | Tony Cingrani | 15 | 2012-2018 | |
| 51 | Hans Crouse# | 15 | 2019-2020 | |
| 51 | Antonio Cruz | 15 | 2014-2014 | |
| 51 | Patrick Etling# | 15 | 2021-2024 | |
| 51 | Ty Harmon# | 15 | 2021-2023 | |
| 51 | John Immerman# | 15 | 2021-2023 | |
| 51 | Dennis Johnston# | 15 | 2017-2021 | |
| 51 | Jason Olbryc# | 15 | 2020-2022 | |
| 51 | Victor Payano# | 15 | 2016-2023 | |
| 51 | Jonathan Perez# | 15 | 2012-2021 | |
| 51 | Michael Wacha# | 15 | 2013-2014 | |
| 63 | Matt Cavanagh# | 14 | 2021-2022 | |
| 63 | Jack Duffey# | 14 | 2023-2024 | |
| 63 | Bill Hauck# | 14 | 2016-2017 | |
| 63 | Tim James# | 14 | 2016-2018 | |
| 63 | Graham Mertz# | 14 | 2022-2022 | |
| 63 | Gary Reed# | 14 | 2020-2023 | |
| 63 | Ron Sullivan# | 14 | 2020-2023 | |
| 63 | Trey Taylor# | 14 | 2020-2021 | |
| 63 | Ralph Travis# | 14 | 2019-2020 | |
| 72 | Melvin Blake# | 13 | 2014-2014 | |
| 72 | Sean Burke# | 13 | 2023-2024 | |
| 72 | Jonathan Cannon# | 13 | 2022-2023 | |
| 72 | Scott Clark# | 13 | 2013-2014 | |
| 72 | George Dawson# | 13 | 2018-2018 | |
| 72 | Emílio Durango# | 13 | 2019-2024 | |
| 72 | Garrett Gould | 13 | 2012-2012 | |
| 72 | Kevin Klein | 13 | 2016-2019 | |
| 72 | Tyler Matzek | 13 | 2012-2013 | |
| 72 | Luis Meléndez# | 13 | 2022-2024 | |
| 72 | Franklin Perez# | 13 | 2020-2021 | |
| 72 | Tim Pruitt# | 13 | 2021-2024 | |
| 72 | Paris Shewey | 13 | 2014-2015 | |
| 72 | Cody Terry# | 13 | 2018-2019 | |
| 72 | Norberto Vargas# | 13 | 2020-2020 | |
| 72 | Brady White# | 13 | 2021-2024 | |
| 72 | Jake Wong# | 13 | 2020-2021 | |
| 89 | Matthew Allan# | 12 | 2022-2022 | |
| 89 | Juan Alvarado# | 12 | 2018-2018 | |
| 89 | Dean Anderson# | 12 | 2020-2021 | |
| 89 | Brad Ashley# | 12 | 2018-2022 | |
| 89 | César Beltrán# | 12 | 2020-2024 | |
| 89 | Jesse Biddle# | 12 | 2013-2014 | |
| 89 | Brett Cecil | 12 | 2020-2020 | |
| 89 | Landon Donohue# | 12 | 2021-2024 | |
| 89 | Mario Díaz# | 12 | 2019-2022 | |
| 89 | Jackson Holgorsen# | 12 | 2019-2020 | |
| 89 | Dave McClain# | 12 | 2017-2019 | |
| 89 | Willie McTear# | 12 | 2017-2022 |
