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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Richard Rogers# | 29 | 2012-2016 | |
| 2 | Jason Davis# | 22 | 2015-2018 | |
| 2 | Cliff Smith# | 22 | 2012-2016 | |
| 2 | Rob Young# | 22 | 2012-2015 | |
| 5 | Jon Morris# | 21 | 2015-2018 | |
| 5 | Tom O'Day# | 21 | 2012-2016 | |
| 7 | Bob Hill# | 20 | 2016-2018 | |
| 7 | William Howard# | 20 | 2012-2015 | |
| 7 | Kevin Landry# | 20 | 2012-2015 | |
| 7 | Bryan Peterson# | 20 | 2012-2016 | |
| 7 | Jake Robinson# | 20 | 2012-2016 | |
| 12 | Ed Armstrong# | 19 | 2016-2018 | |
| 12 | Rod Crowe# | 19 | 2015-2018 | |
| 12 | Carlos Díaz# | 19 | 2012-2015 | |
| 12 | John Jones# | 19 | 2012-2016 | |
| 12 | Bob Moore# | 19 | 2012-2015 | |
| 12 | Félix Ortíz# | 19 | 2012-2015 | |
| 12 | Howard Poole# | 19 | 2016-2018 | |
| 12 | John Slater# | 19 | 2014-2017 | |
| 20 | Tommy Bartlett# | 18 | 2015-2018 | |
| 20 | Pedro Díaz# | 18 | 2012-2016 | |
| 20 | Jesús Feliciano# | 18 | 2012-2015 | |
| 20 | Luis Fuentes# | 18 | 2012-2014 | |
| 20 | Christian Harris# | 18 | 2013-2016 | |
| 20 | Ed Lott# | 18 | 2012-2015 | |
| 20 | Juan Mendoza# | 18 | 2012-2015 | |
| 20 | Pancho Romero# | 18 | 2012-2014 | |
| 20 | Carlos Ruíz# | 18 | 2012-2015 | |
| 29 | Jude Anderson# | 17 | 2016-2018 | |
| 29 | Troy Davis# | 17 | 2012-2016 | |
| 29 | José Delgado# | 17 | 2012-2015 | |
| 29 | Eric Edwards# | 17 | 2016-2018 | |
| 29 | Robinson García# | 17 | 2012-2016 | |
| 29 | Jorge Hernández# | 17 | 2012-2014 | |
| 29 | Jonathan Martin# | 17 | 2012-2015 | |
| 29 | Joël Mastroianni# | 17 | 2012-2014 | |
| 29 | James Phillips# | 17 | 2012-2014 | |
| 29 | Daniel Román | 17 | 2012-2014 | |
| 29 | Richard Stevenson# | 17 | 2012-2015 | |
| 29 | Bubba Thompson# | 17 | 2012-2015 | |
| 41 | Tony Baltiérrez# | 16 | 2015-2018 | |
| 41 | John Cannon# | 16 | 2013-2016 | |
| 41 | Jonathan Clark# | 16 | 2015-2018 | |
| 41 | Theodore Foster# | 16 | 2012-2015 | |
| 41 | Paul Johnston# | 16 | 2012-2013 | |
| 41 | Jesús Ortíz# | 16 | 2012-2016 | |
| 41 | Curt Rhodes# | 16 | 2012-2015 | |
| 41 | Fabián Torres# | 16 | 2012-2014 | |
| 41 | Ray Weeks# | 16 | 2016-2018 | |
| 41 | David White# | 16 | 2012-2014 | |
| 41 | Buddy Wills# | 16 | 2012-2013 | |
| 52 | Jason Adams# | 15 | 2012-2014 | |
| 52 | Jeffrey Allison# | 15 | 2015-2018 | |
| 52 | Eric Billings# | 15 | 2015-2018 | |
| 52 | Román Cruz# | 15 | 2016-2018 | |
| 52 | Bill Dillard# | 15 | 2013-2016 | |
| 52 | Jason Foster# | 15 | 2016-2018 | |
| 52 | Lewis Hunter# | 15 | 2014-2017 | |
| 52 | Jason Lambright | 15 | 2012-2016 | |
| 52 | Dave Meriken | 15 | 2012-2015 | |
| 52 | António Navarro# | 15 | 2016-2018 | |
| 52 | Aaron Simmons# | 15 | 2012-2015 | |
| 52 | Mark Stevenson# | 15 | 2015-2018 | |
| 52 | Doug Walsh# | 15 | 2012-2014 | |
| 65 | Larry Anderson# | 14 | 2012-2015 | |
| 65 | Joe Bascombe# | 14 | 2015-2018 | |
| 65 | William Brooks# | 14 | 2013-2015 | |
| 65 | Ramón Castaneda# | 14 | 2012-2014 | |
| 65 | Jesús Castillo# | 14 | 2015-2018 | |
| 65 | Stan Crocker# | 14 | 2016-2018 | |
| 65 | Robert Dunn# | 14 | 2015-2018 | |
| 65 | Tim Fowler# | 14 | 2012-2015 | |
| 65 | Juan García# | 14 | 2015-2018 | |
| 65 | Matt Jenkins | 14 | 2012-2015 | |
| 65 | Ryan Jenkins# | 14 | 2012-2015 | |
| 65 | Leonard Jones# | 14 | 2015-2017 | |
| 65 | John Keith# | 14 | 2014-2017 | |
| 65 | Jayson Moore# | 14 | 2012-2014 | |
| 65 | Chuck Noblet# | 14 | 2014-2017 | |
| 65 | Adrián Orozco# | 14 | 2012-2014 | |
| 65 | Jesús Ramírez# | 14 | 2012-2015 | |
| 65 | Pepe Vargas# | 14 | 2015-2018 | |
| 65 | Ramón Vázquez# | 14 | 2012-2014 | |
| 65 | Tim Walker# | 14 | 2017-2018 | |
| 65 | Will Wood# | 14 | 2012-2016 | |
| 86 | Mark Atkins# | 13 | 2015-2018 | |
| 86 | Shane Becker# | 13 | 2012-2015 | |
| 86 | Fred Butler# | 13 | 2012-2014 | |
| 86 | Robbie Cannon# | 13 | 2016-2018 | |
| 86 | Bill Clay# | 13 | 2012-2015 | |
| 86 | Carl Clay# | 13 | 2014-2016 | |
| 86 | Jason Collins# | 13 | 2012-2014 | |
| 86 | Beau Davies# | 13 | 2016-2018 | |
| 86 | Trip Finch# | 13 | 2012-2015 | |
| 86 | Todd Green# | 13 | 2014-2017 | |
| 86 | Jim Hall# | 13 | 2012-2015 | |
| 86 | Zeus Hallman# | 13 | 2014-2016 | |
| 86 | Stephen Harding# | 13 | 2016-2018 | |
| 86 | Fred Hess | 13 | 2012-2015 | |
| 86 | Johnny Jacobs# | 13 | 2014-2017 |
