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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Javier Mejía# | 28 | 2012-2016 | |
| 2 | Roy Offerman# | 13 | 2018-2021 | |
| 3 | Jesús Estrada# | 12 | 2018-2021 | |
| 3 | Joe Pagán# | 12 | 2017-2019 | |
| 5 | Matthew Duncan# | 11 | 2020-2022 | |
| 5 | Jason Groome# | 11 | 2017-2018 | |
| 5 | Alfredo Sepúlveda# | 11 | 2019-2021 | |
| 5 | Nick Travieso | 11 | 2012-2013 | |
| 5 | Brock Young# | 11 | 2012-2014 | |
| 10 | Tyler Byrne# | 10 | 2017-2020 | |
| 10 | Brad Dale# | 10 | 2018-2018 | |
| 10 | Nolan Green# | 10 | 2017-2019 | |
| 10 | Mario Martínez# | 10 | 2019-2020 | |
| 10 | Lance McCullers# | 10 | 2012-2013 | |
| 10 | Payton Thorne# | 10 | 2019-2021 | |
| 16 | Jesús Acosta# | 9 | 2019-2021 | |
| 16 | Lorne Critch# | 9 | 2019-2020 | |
| 16 | Duncan Duimelaar# | 9 | 2017-2017 | |
| 16 | Raymond Lonsber# | 9 | 2018-2020 | |
| 16 | Chase Petty# | 9 | 2021-2022 | |
| 16 | Miguel Pineda# | 9 | 2012-2013 | |
| 16 | Fernando Pérez# | 9 | 2018-2020 | |
| 16 | Tate Rodemaker# | 9 | 2020-2021 | |
| 16 | Tristan Stobbie# | 9 | 2017-2019 | |
| 16 | Marc Thompson# | 9 | 2017-2019 | |
| 26 | Kong Chen# | 8 | 2017-2018 | |
| 26 | Roberto Collazo# | 8 | 2018-2020 | |
| 26 | Dave Lloyd# | 8 | 2017-2019 | |
| 26 | Ray Moody# | 8 | 2017-2018 | |
| 26 | Jesse Patterson# | 8 | 2017-2018 | |
| 26 | Cole Wilcox# | 8 | 2018-2018 | |
| 32 | Fortunato Atansio# | 7 | 2021-2022 | |
| 32 | Ben Camp# | 7 | 2017-2017 | |
| 32 | Lou Cooper# | 7 | 2017-2018 | |
| 32 | Gilberto Fernández# | 7 | 2017-2020 | |
| 32 | John Gant# | 7 | 2012-2013 | |
| 32 | Ed Goff# | 7 | 2020-2021 | |
| 32 | Gunnar Graham# | 7 | 2020-2020 | |
| 32 | Hunter Greene# | 7 | 2018-2018 | |
| 32 | Clayton Kwiatkowski# | 7 | 2020-2021 | |
| 32 | Jack Lewis# | 7 | 2019-2019 | |
| 32 | Seth Lonsway# | 7 | 2020-2020 | |
| 32 | Scott Meeligan# | 7 | 2017-2017 | |
| 32 | Craig Missigman# | 7 | 2012-2013 | |
| 32 | Paul Orr# | 7 | 2014-2015 | |
| 32 | Tyler Owens# | 7 | 2019-2019 | |
| 32 | Carlos Pina# | 7 | 2012-2012 | |
| 32 | Jean-Luc Raymond# | 7 | 2013-2014 | |
| 32 | Nick Thwaits# | 7 | 2021-2021 | |
| 32 | Kaong Weng# | 7 | 2021-2022 | |
| 51 | Robin Addison# | 6 | 2017-2019 | |
| 51 | Philip Anderson# | 6 | 2021-2021 | |
| 51 | Tanner Bailey# | 6 | 2022-2022 | |
| 51 | Jay Black# | 6 | 2022-2022 | |
| 51 | Don Butt# | 6 | 2019-2022 | |
| 51 | Adrián Castillo# | 6 | 2013-2015 | |
| 51 | Andy Cox# | 6 | 2017-2017 | |
| 51 | Chris Cox# | 6 | 2013-2016 | |
| 51 | Jack Curtis# | 6 | 2017-2020 | |
| 51 | Dan Dukes | 6 | 2014-2014 | |
| 51 | Orlando Días# | 6 | 2013-2015 | |
| 51 | Kurt Estil# | 6 | 2021-2022 | |
| 51 | Chris Farrell | 6 | 2013-2013 | |
| 51 | Jackson Finley# | 6 | 2022-2022 | |
| 51 | Jose R. Flores | 6 | 2013-2013 | |
| 51 | Ricardo Galván# | 6 | 2019-2020 | |
| 51 | Domingo González# | 6 | 2019-2020 | |
| 51 | Victor Gustafson# | 6 | 2013-2015 | |
| 51 | Martin Heinrich# | 6 | 2017-2018 | |
| 51 | Thomas Hershiser# | 6 | 2021-2021 | |
| 51 | Eli Jerzembeck# | 6 | 2022-2022 | |
| 51 | Jace Johnson# | 6 | 2022-2022 | |
| 51 | Kevin Louden# | 6 | 2020-2021 | |
| 51 | José López# | 6 | 2021-2021 | |
| 51 | Carlos Martínez# | 6 | 2020-2021 | |
| 51 | Billy Mooney# | 6 | 2018-2019 | |
| 51 | Hayden Mullins# | 6 | 2020-2020 | |
| 51 | Marcos Márquez# | 6 | 2018-2019 | |
| 51 | Juan Méndez# | 6 | 2020-2021 | |
| 51 | Pat Olson# | 6 | 2018-2019 | |
| 51 | Teo Ottenhof# | 6 | 2013-2015 | |
| 51 | Jay Pate# | 6 | 2021-2022 | |
| 51 | Kilby Pena# | 6 | 2012-2013 | |
| 51 | Curtis Peters# | 6 | 2014-2015 | |
| 51 | Riley Pint# | 6 | 2017-2018 | |
| 51 | José Pérez# | 6 | 2021-2022 | |
| 51 | José Ramos# | 6 | 2021-2022 | |
| 51 | Joe Rock# | 6 | 2021-2022 | |
| 51 | Kumar Rocker# | 6 | 2018-2018 | |
| 51 | Miguel Romano# | 6 | 2022-2022 | |
| 51 | Matthew Smoral# | 6 | 2012-2013 | |
| 51 | Jesús Soto# | 6 | 2019-2019 | |
| 51 | Alvin Tigner# | 6 | 2021-2021 | |
| 51 | Mark Walls# | 6 | 2021-2022 | |
| 51 | Aaron Wright# | 6 | 2017-2019 | |
| 96 | Joe Austin# | 5 | 2015-2015 | |
| 96 | Tanner Bibee# | 5 | 2020-2020 | |
| 96 | Manuel Borrayo# | 5 | 2022-2022 | |
| 96 | Torquato Britschgi# | 5 | 2021-2021 | |
| 96 | Aaron Brown# | 5 | 2021-2022 |
