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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Clay Clark# | 28 | 2015-2018 | |
| 2 | Brent Riley# | 26 | 2015-2019 | |
| 3 | Ray Thibaut# | 22 | 2015-2019 | |
| 3 | Steven Williams# | 22 | 2015-2019 | |
| 5 | Jesús López# | 21 | 2016-2019 | |
| 5 | Bob McGhee# | 21 | 2015-2019 | |
| 7 | Emory Bryant# | 20 | 2015-2019 | |
| 8 | Ken Carter# | 19 | 2015-2016 | |
| 8 | Josh Gardner# | 19 | 2017-2019 | |
| 10 | Greg Kelly# | 18 | 2016-2019 | |
| 10 | Alonso Rodríguez# | 18 | 2015-2019 | |
| 12 | Xavier Andrade# | 17 | 2017-2019 | |
| 12 | Luis Fernández# | 17 | 2015-2016 | |
| 12 | Teddy Jones# | 17 | 2017-2019 | |
| 12 | Paul Nance# | 17 | 2015-2016 | |
| 12 | José Rodríguez# | 17 | 2015-2019 | |
| 12 | Artie Taylor# | 17 | 2017-2018 | |
| 12 | José Trujillo# | 17 | 2016-2019 | |
| 12 | Louis Webber# | 17 | 2016-2019 | |
| 20 | Nick Blount# | 16 | 2016-2019 | |
| 20 | Robert Byrd# | 16 | 2017-2019 | |
| 20 | Iván Castillo# | 16 | 2015-2018 | |
| 20 | Homer Shafer# | 16 | 2015-2019 | |
| 24 | Anthony Hanover# | 15 | 2016-2019 | |
| 24 | Leroy Picot# | 15 | 2018-2019 | |
| 24 | Jorge Rivas# | 15 | 2017-2019 | |
| 27 | Mackenzie Bolen# | 14 | 2015-2018 | |
| 27 | John Boyle# | 14 | 2017-2019 | |
| 27 | Hubert Dunham# | 14 | 2016-2019 | |
| 27 | César García# | 14 | 2016-2018 | |
| 27 | Doug Green# | 14 | 2018-2019 | |
| 27 | Andrew Hayes# | 14 | 2016-2019 | |
| 27 | Miguel López# | 14 | 2015-2018 | |
| 27 | Dave Mitchell# | 14 | 2017-2019 | |
| 27 | Eric Patnode# | 14 | 2016-2019 | |
| 27 | Iván Román# | 14 | 2016-2018 | |
| 27 | Alfredo Torres# | 14 | 2015-2019 | |
| 27 | Ayres Valido# | 14 | 2015-2019 | |
| 27 | Pancho Vargas# | 14 | 2015-2019 | |
| 27 | Bob Warford# | 14 | 2017-2018 | |
| 27 | Jimmy Wilson# | 14 | 2016-2017 | |
| 42 | John Ashley# | 13 | 2017-2019 | |
| 42 | Francisco Barrios# | 13 | 2016-2018 | |
| 42 | Woody Carlson# | 13 | 2018-2019 | |
| 42 | Freddy González# | 13 | 2015-2019 | |
| 42 | Anthony Graham# | 13 | 2017-2019 | |
| 42 | Morris Nicholson# | 13 | 2015-2016 | |
| 42 | Homer O'Lannigan# | 13 | 2018-2019 | |
| 42 | Branislav Stankovic# | 13 | 2016-2019 | |
| 50 | Art Adams# | 12 | 2015-2016 | |
| 50 | Ed Day# | 12 | 2018-2019 | |
| 50 | Gregory Gary# | 12 | 2015-2017 | |
| 50 | Samuel Hawkins# | 12 | 2015-2018 | |
| 50 | Justin Jamerson# | 12 | 2015-2019 | |
| 50 | Manuel Ortíz# | 12 | 2016-2019 | |
| 50 | Doruk Oyan# | 12 | 2015-2019 | |
| 50 | Allen Wilson# | 12 | 2016-2017 | |
| 50 | Brad Wilson# | 12 | 2015-2019 | |
| 59 | Elvin Brooks# | 11 | 2015-2017 | |
| 59 | Sam Cobb# | 11 | 2017-2019 | |
| 59 | Pedro Feliciano# | 11 | 2016-2018 | |
| 59 | Tom Hernández# | 11 | 2016-2019 | |
| 59 | Andrés Martínez# | 11 | 2016-2017 | |
| 59 | Jeff Mayer# | 11 | 2018-2019 | |
| 59 | John Stone# | 11 | 2015-2018 | |
| 59 | Mark Tucker# | 11 | 2017-2019 | |
| 59 | Wally Wilkerson# | 11 | 2018-2019 | |
| 68 | Dan Boyle# | 10 | 2015-2019 | |
| 68 | Dave Davis# | 10 | 2017-2018 | |
| 68 | Robinson Gonzáles# | 10 | 2017-2019 | |
| 68 | Peyton Leach# | 10 | 2016-2018 | |
| 68 | Juan López# | 10 | 2017-2018 | |
| 68 | Alfredo Martínez# | 10 | 2017-2019 | |
| 68 | Louis McDowell# | 10 | 2015-2018 | |
| 68 | Steve Pérez# | 10 | 2015-2019 | |
| 68 | John Shirley# | 10 | 2018-2019 | |
| 68 | Ben Smith# | 10 | 2017-2019 | |
| 68 | Vernon Turner# | 10 | 2018-2019 | |
| 79 | John Adams# | 9 | 2016-2019 | |
| 79 | Arnaldo Bodabalho# | 9 | 2019-2019 | |
| 79 | Richard Brown# | 9 | 2015-2019 | |
| 79 | Billy Bruce# | 9 | 2017-2018 | |
| 79 | Álex Carrillo# | 9 | 2018-2019 | |
| 79 | César Díaz# | 9 | 2017-2018 | |
| 79 | Eduardo Estrada# | 9 | 2015-2019 | |
| 79 | Michael Fields# | 9 | 2015-2019 | |
| 79 | Alonso García# | 9 | 2016-2019 | |
| 79 | Tim Holmes | 9 | 2015-2016 | |
| 79 | Pat McCormick# | 9 | 2018-2019 | |
| 79 | Richard Meyer# | 9 | 2017-2017 | |
| 79 | Ramón Molina# | 9 | 2015-2017 | |
| 79 | Luis Oliva# | 9 | 2017-2019 | |
| 79 | Álex Padilla# | 9 | 2017-2018 | |
| 79 | Mike Russell# | 9 | 2018-2019 | |
| 79 | Wilson Vélez# | 9 | 2016-2019 | |
| 79 | Stanley Williams# | 9 | 2015-2016 | |
| 79 | Henry Yates# | 9 | 2019-2019 | |
| 98 | Rafael Chávez# | 8 | 2015-2016 | |
| 98 | Rafael Flores# | 8 | 2017-2019 | |
| 98 | Phil Frost# | 8 | 2016-2019 |
