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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Frank Leshane# | 79 | 2049-2065 | |
| 2 | Sergio Báez# | 72 | 2057-2065 | |
| 3 | Alan Payne# | 61 | 2053-2065 | |
| 3 | Randy Tyack# | 61 | 2055-2065 | |
| 5 | Rob Taylor# | 57 | 2054-2065 | |
| 6 | Dan Leighburn# | 55 | 2049-2065 | |
| 6 | Pat Snyder# | 55 | 2054-2065 | |
| 8 | José Silva | 52 | 2049-2054 | |
| 9 | Dave Wray# | 50 | 2056-2065 | |
| 10 | Mehdi Chaumont# | 49 | 2057-2065 | |
| 10 | Ted Dunn# | 49 | 2054-2065 | |
| 10 | Brad Lewis# | 49 | 2057-2065 | |
| 10 | Angelo Nicoli# | 49 | 2057-2065 | |
| 10 | César Sandoval | 49 | 2049-2054 | |
| 15 | Darren Elmore# | 48 | 2050-2065 | |
| 15 | Edgar Ramírez# | 48 | 2055-2065 | |
| 17 | Ki-moon Kang# | 47 | 2056-2065 | |
| 17 | Manny López# | 47 | 2050-2065 | |
| 17 | Cisco Soto# | 47 | 2056-2065 | |
| 20 | Carlos Bonilla# | 46 | 2057-2065 | |
| 20 | Albert Varela# | 46 | 2056-2065 | |
| 22 | Christian Hunt# | 45 | 2053-2065 | |
| 22 | Artie Pursglove# | 45 | 2053-2065 | |
| 24 | Louis Jeffery# | 44 | 2052-2064 | |
| 24 | Edmund Vickers | 44 | 2057-2063 | |
| 26 | José Cruz# | 43 | 2055-2065 | |
| 26 | Albert Elías# | 43 | 2059-2065 | |
| 26 | Bob Newman# | 43 | 2057-2065 | |
| 29 | Juan Castano# | 42 | 2055-2065 | |
| 29 | Chris Murphy# | 42 | 2053-2065 | |
| 29 | José Sánchez# | 42 | 2058-2065 | |
| 29 | Ron Ward# | 42 | 2060-2065 | |
| 29 | Toshimichi Yoshida# | 42 | 2058-2065 | |
| 34 | Dale Buda# | 41 | 2055-2065 | |
| 34 | Rodrigo Martínez | 41 | 2052-2058 | |
| 34 | Mike Patterson# | 41 | 2056-2065 | |
| 34 | Phil Stoddart# | 41 | 2054-2065 | |
| 38 | Daniel Parra# | 40 | 2055-2065 | |
| 38 | Eddie Sierra# | 40 | 2052-2065 | |
| 40 | Bob Fisher# | 39 | 2057-2065 | |
| 40 | Doug Garland# | 39 | 2059-2065 | |
| 40 | Trevor Huddleston# | 39 | 2061-2065 | |
| 43 | Steve Allen# | 38 | 2053-2065 | |
| 43 | Joel Augustus# | 38 | 2061-2064 | |
| 43 | Jeremy Bates# | 38 | 2062-2065 | |
| 43 | Joe Floyd# | 38 | 2062-2065 | |
| 43 | Rob Pate# | 38 | 2051-2063 | |
| 43 | Augusto Ramos | 38 | 2051-2059 | |
| 43 | Jimmy Sheehan | 38 | 2058-2062 | |
| 43 | Jorge Suárez# | 38 | 2057-2065 | |
| 43 | Shoda Tanaka# | 38 | 2061-2065 | |
| 52 | Vic Foster# | 37 | 2061-2065 | |
| 52 | Jorge Serrano# | 37 | 2061-2065 | |
| 54 | Ron Hammond# | 36 | 2055-2065 | |
| 54 | Charlie Hardy# | 36 | 2055-2063 | |
| 54 | Brian Heinz# | 36 | 2055-2065 | |
| 54 | Daniel Martínez# | 36 | 2050-2065 | |
| 58 | Kyle Lynch# | 35 | 2053-2065 | |
| 58 | Ken Meadows | 35 | 2057-2065 | |
| 58 | Hank Rainey# | 35 | 2059-2065 | |
| 58 | Ben Williams# | 35 | 2056-2065 | |
| 62 | José Corona# | 34 | 2060-2065 | |
| 62 | Joe Engstrom | 34 | 2051-2064 | |
| 62 | Christopher Hoffmann# | 34 | 2059-2063 | |
| 62 | Pete Rodriguez# | 34 | 2056-2065 | |
| 62 | Dustin van de Velde# | 34 | 2058-2065 | |
| 62 | Waylon Williams# | 34 | 2057-2065 | |
| 62 | Artie Woods# | 34 | 2061-2065 | |
| 69 | Kevin Dunn | 33 | 2057-2063 | |
| 69 | José Estrada# | 33 | 2055-2065 | |
| 69 | Jimmy Shepard# | 33 | 2056-2065 | |
| 69 | Josh Singleton# | 33 | 2062-2065 | |
| 73 | Noah Krause# | 32 | 2058-2065 | |
| 73 | Dave Little | 32 | 2056-2063 | |
| 73 | Chad MacPherson# | 32 | 2060-2065 | |
| 73 | Bret McIlherne | 32 | 2059-2064 | |
| 73 | Del Payton# | 32 | 2056-2065 | |
| 73 | Ánibal Sánchez | 32 | 2057-2060 | |
| 73 | Luis Zepeda# | 32 | 2058-2065 | |
| 80 | Edwin Castro# | 31 | 2056-2065 | |
| 80 | Kip Gray# | 31 | 2057-2065 | |
| 80 | Craig Hathorn# | 31 | 2055-2065 | |
| 80 | Shawn O'Reilly | 31 | 2054-2062 | |
| 80 | Mal Walter# | 31 | 2057-2062 | |
| 85 | Osano Abeeku# | 30 | 2057-2063 | |
| 85 | Víctor Alvarado# | 30 | 2058-2065 | |
| 85 | Luis Ayala# | 30 | 2063-2065 | |
| 85 | Brian Hough# | 30 | 2061-2065 | |
| 85 | Josh Lowder# | 30 | 2056-2065 | |
| 85 | Jesús Mercado# | 30 | 2062-2065 | |
| 85 | Ruben Pabon# | 30 | 2059-2065 | |
| 85 | Chris Pegram# | 30 | 2055-2065 | |
| 85 | Matt Shook# | 30 | 2055-2062 | |
| 94 | Zach Boswell# | 29 | 2062-2065 | |
| 94 | Juan Contreras# | 29 | 2063-2065 | |
| 94 | Bob Ellis# | 29 | 2062-2065 | |
| 94 | Edwin Hoekstra# | 29 | 2057-2065 | |
| 94 | John Hussey# | 29 | 2053-2062 | |
| 94 | Luis Ibarra# | 29 | 2058-2065 | |
| 94 | Frank Martin# | 29 | 2058-2065 |
