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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Maurice Gould# | 122 | 2012-2017 | |
| 2 | Raúl Pérez# | 106 | 2012-2017 | |
| 3 | Nolan Lyons# | 96 | 2012-2017 | |
| 4 | Wilfred Brooks# | 93 | 2012-2017 | |
| 4 | Roberto Martínez# | 93 | 2012-2017 | |
| 6 | António Gómez# | 87 | 2012-2017 | |
| 7 | Rich Bussell# | 84 | 2012-2017 | |
| 7 | Charles Luce# | 84 | 2012-2017 | |
| 9 | Aurelio Ramírez# | 83 | 2012-2017 | |
| 9 | Nathan Wilson# | 83 | 2012-2017 | |
| 11 | Kent Rose# | 81 | 2012-2017 | |
| 12 | Kevin Sampson# | 80 | 2012-2017 | |
| 13 | Manuel Ruíz# | 78 | 2012-2017 | |
| 14 | Austin Brown# | 77 | 2012-2017 | |
| 15 | Jim Brady# | 74 | 2012-2017 | |
| 15 | Davey Holmes# | 74 | 2012-2017 | |
| 17 | Adam Thomas# | 70 | 2012-2017 | |
| 17 | Evan Warner# | 70 | 2012-2017 | |
| 19 | Rodney Armstrong# | 69 | 2012-2017 | |
| 20 | Stephen Lawrence# | 68 | 2012-2017 | |
| 20 | Rafael López# | 68 | 2012-2017 | |
| 22 | Norm Jackson# | 67 | 2012-2017 | |
| 22 | Dave Lee# | 67 | 2012-2017 | |
| 22 | Bob Magee# | 67 | 2012-2017 | |
| 25 | Elvis Sharp# | 66 | 2012-2017 | |
| 26 | Ray Larson# | 64 | 2012-2017 | |
| 27 | Royce Butterfield# | 63 | 2012-2017 | |
| 27 | Ray Clay# | 63 | 2012-2017 | |
| 27 | Edward Griffith# | 63 | 2012-2017 | |
| 30 | Jim Fleming# | 61 | 2012-2017 | |
| 31 | Pat Everhart# | 60 | 2012-2017 | |
| 32 | Ángel Galindo# | 59 | 2012-2017 | |
| 33 | Dave Nicholson# | 58 | 2012-2017 | |
| 34 | Jason Bolyard# | 56 | 2012-2016 | |
| 34 | Michael Henderson# | 56 | 2012-2017 | |
| 34 | Brian Hudson# | 56 | 2012-2017 | |
| 34 | Bob Lee# | 56 | 2012-2017 | |
| 34 | Mike Miller# | 56 | 2012-2017 | |
| 39 | Terence McKinley# | 55 | 2013-2017 | |
| 39 | Tony Ross | 55 | 2012-2016 | |
| 41 | Tom Owens# | 54 | 2012-2017 | |
| 41 | Derrick Scott# | 54 | 2014-2017 | |
| 43 | Jesse George# | 53 | 2012-2017 | |
| 44 | José Serrano# | 51 | 2012-2017 | |
| 45 | Fraser Crawford# | 50 | 2012-2017 | |
| 45 | Arthur Gardner# | 50 | 2012-2016 | |
| 47 | Paul Johnston# | 49 | 2014-2017 | |
| 47 | Chris Wine# | 49 | 2012-2017 | |
| 49 | Jake Nelson# | 48 | 2012-2017 | |
| 49 | Jeremy Rogers# | 48 | 2012-2016 | |
| 49 | Bob Williams# | 48 | 2012-2017 | |
| 52 | Michael Bryan# | 46 | 2012-2017 | |
| 52 | Pat Heard# | 46 | 2012-2017 | |
| 52 | Jim Thompson | 46 | 2012-2016 | |
| 55 | Javier Flores | 45 | 2012-2016 | |
| 55 | Mike Joyce# | 45 | 2012-2017 | |
| 55 | Ricky Smith# | 45 | 2012-2016 | |
| 58 | Brad Anderson# | 44 | 2012-2016 | |
| 58 | Scott Wilson# | 44 | 2014-2017 | |
| 60 | Franklin Cox# | 43 | 2012-2017 | |
| 60 | James Dooley# | 43 | 2012-2017 | |
| 60 | Cecil Gibbons# | 43 | 2012-2017 | |
| 60 | Bob Rudyard | 43 | 2012-2015 | |
| 64 | Anthony Atkinson# | 42 | 2013-2017 | |
| 64 | Roberto González# | 42 | 2012-2017 | |
| 64 | Sixto Lavio# | 42 | 2012-2017 | |
| 64 | Ray Lester# | 42 | 2012-2017 | |
| 64 | Martin Merritt# | 42 | 2013-2017 | |
| 69 | Roberto Campos# | 41 | 2012-2017 | |
| 69 | Travis James | 41 | 2012-2015 | |
| 69 | Joe Russell# | 41 | 2012-2017 | |
| 72 | Kevin Black# | 40 | 2012-2016 | |
| 72 | Juan Fernández# | 40 | 2012-2016 | |
| 72 | Pat Sellers | 40 | 2012-2015 | |
| 72 | Gerald Webb# | 40 | 2013-2017 | |
| 76 | Charles Bailey# | 39 | 2013-2017 | |
| 76 | Rich Barrett# | 39 | 2012-2017 | |
| 76 | Tom Bray# | 39 | 2012-2017 | |
| 76 | Jimmy Drake# | 39 | 2012-2016 | |
| 76 | Lou Smith# | 39 | 2012-2017 | |
| 76 | Homer Turner# | 39 | 2012-2017 | |
| 82 | Matt Walton# | 38 | 2012-2017 | |
| 83 | Troy Baker# | 37 | 2012-2017 | |
| 83 | Cohen Brouillette# | 37 | 2015-2017 | |
| 83 | Javier Solís# | 37 | 2012-2017 | |
| 83 | Keith Thompson# | 37 | 2012-2017 | |
| 87 | Nelson Ingram# | 36 | 2012-2016 | |
| 87 | Jorge Mendoza# | 36 | 2012-2017 | |
| 87 | Brandon Wilson# | 36 | 2012-2017 | |
| 90 | Chase Burke# | 35 | 2012-2017 | |
| 90 | Robert Cates# | 35 | 2012-2017 | |
| 90 | Glenn Floyd# | 35 | 2013-2017 | |
| 90 | Joe McDowell# | 35 | 2012-2017 | |
| 90 | Larry Smiley | 35 | 2012-2015 | |
| 90 | Jeremy Woods# | 35 | 2013-2017 | |
| 96 | Dennis Inman# | 34 | 2012-2017 | |
| 96 | Steve Johnson# | 34 | 2012-2017 | |
| 96 | Peter Klein# | 34 | 2012-2017 | |
| 96 | Aurelio Mata# | 34 | 2012-2017 | |
| 96 | William Nolan# | 34 | 2012-2017 |
