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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Ariel Robinson# | 9 | 2038-2050 | |
| 2 | Greyson Tadic# | 6 | 2048-2050 | |
| 3 | C.J. Brisset# | 5 | 2048-2050 | |
| 3 | Sean Dickey# | 5 | 2048-2050 | |
| 3 | Vincent Dion# | 5 | 2038-2050 | |
| 3 | Mick Griffis# | 5 | 2045-2050 | |
| 3 | Charles Lupa# | 5 | 2046-2050 | |
| 3 | Shay Merida# | 5 | 2047-2050 | |
| 9 | Lincoln Anderson# | 4 | 2044-2050 | |
| 9 | Edgard Baez# | 4 | 2047-2049 | |
| 9 | Antonio Cardenas | 4 | 2031-2046 | |
| 9 | Parker Cassidy# | 4 | 2039-2050 | |
| 9 | Henry Colon | 4 | 2032-2048 | |
| 9 | Juan Flores# | 4 | 2041-2050 | |
| 9 | Mathew Haggerty | 4 | 2034-2045 | |
| 9 | Jimeno Heredia# | 4 | 2039-2048 | |
| 9 | Rob Long# | 4 | 2042-2049 | |
| 9 | Cullen O'Neill | 4 | 2038-2048 | |
| 9 | Frans Parish# | 4 | 2043-2050 | |
| 9 | Curt Peterson# | 4 | 2047-2048 | |
| 9 | Rob Provo | 4 | 2039-2050 | |
| 9 | Barry Spencer# | 4 | 2042-2049 | |
| 23 | Sean Addington | 3 | 2035-2047 | |
| 23 | Weston Barnett# | 3 | 2046-2049 | |
| 23 | Dan Bower# | 3 | 2046-2050 | |
| 23 | Chris Braden | 3 | 2028-2039 | |
| 23 | William Britt# | 3 | 2040-2050 | |
| 23 | Rowen Carnicom# | 3 | 2043-2050 | |
| 23 | Bruno Chili | 3 | 2037-2040 | |
| 23 | Smokey Deveraux# | 3 | 2049-2050 | |
| 23 | Graham Doss# | 3 | 2050-2050 | |
| 23 | Andrew Dunbar# | 3 | 2043-2047 | |
| 23 | Johnny Farrington# | 3 | 2037-2048 | |
| 23 | Cayden Finnerty | 3 | 2039-2050 | |
| 23 | Graham Gal# | 3 | 2048-2050 | |
| 23 | Tony Gonzalez | 3 | 2029-2042 | |
| 23 | Junior Grant | 3 | 2037-2047 | |
| 23 | Ian Gutenberg | 3 | 2037-2048 | |
| 23 | Owen Holiday# | 3 | 2049-2050 | |
| 23 | Jacob Huggins# | 3 | 2043-2049 | |
| 23 | Evan Jean | 3 | 2039-2042 | |
| 23 | Jonah Kraemer | 3 | 2033-2047 | |
| 23 | Robert Lacoste# | 3 | 2046-2048 | |
| 23 | Id Lesher# | 3 | 2038-2049 | |
| 23 | Hugo Luevano# | 3 | 2049-2050 | |
| 23 | Sergio Marrero | 3 | 2032-2045 | |
| 23 | Nick Moffat | 3 | 2029-2038 | |
| 23 | D.J. Newton# | 3 | 2036-2050 | |
| 23 | Starling Peña# | 3 | 2036-2050 | |
| 23 | Jason Phillips# | 3 | 2046-2048 | |
| 23 | Carlos Polanco | 3 | 2033-2049 | |
| 23 | Perfecto Polanco# | 3 | 2047-2050 | |
| 23 | Jim Reed# | 3 | 2039-2050 | |
| 23 | Jimmy Robinson | 3 | 2035-2047 | |
| 23 | Che-Ming Shieh# | 3 | 2045-2048 | |
| 23 | Mick Simmons# | 3 | 2042-2050 | |
| 23 | Tony Tom | 3 | 2038-2049 | |
| 23 | Niles Valencia# | 3 | 2041-2050 | |
| 23 | Hunter Vandi# | 3 | 2039-2050 | |
| 23 | Erinyo Zamarripa# | 3 | 2050-2050 | |
| 61 | Ted Abreu# | 2 | 2050-2050 | |
| 61 | Harvey Allison# | 2 | 2040-2047 | |
| 61 | Todd Avery | 2 | 2036-2049 | |
| 61 | Richard Beaty# | 2 | 2046-2049 | |
| 61 | Noah Bennett | 2 | 2033-2043 | |
| 61 | Yadiel Berroa# | 2 | 2044-2050 | |
| 61 | Terence Blevins# | 2 | 2040-2050 | |
| 61 | Gaetano Bowers# | 2 | 2046-2046 | |
| 61 | DeWayne Bowles | 2 | 2035-2040 | |
| 61 | Noel Burkhart | 2 | 2036-2046 | |
| 61 | Matt Chambers | 2 | 2030-2041 | |
| 61 | Bob Charles# | 2 | 2046-2050 | |
| 61 | Christian Coaty | 2 | 2032-2041 | |
| 61 | Quincy Cordell | 2 | 2042-2042 | |
| 61 | Edwin De Soto# | 2 | 2049-2049 | |
| 61 | Royce Dovin# | 2 | 2050-2050 | |
| 61 | Júlio Díaz# | 2 | 2047-2050 | |
| 61 | Liam Eachus | 2 | 2033-2042 | |
| 61 | Albertin Estrada | 2 | 2037-2050 | |
| 61 | Gilberto Etcheverry# | 2 | 2048-2048 | |
| 61 | Da'Shawn Evans# | 2 | 2041-2043 | |
| 61 | Jon Fillion | 2 | 2036-2048 | |
| 61 | Joshua Finau# | 2 | 2036-2050 | |
| 61 | Salvador Franchini# | 2 | 2049-2050 | |
| 61 | Fabian Galloway# | 2 | 2047-2049 | |
| 61 | Tomas Garza# | 2 | 2041-2050 | |
| 61 | Ethan Gasbarre# | 2 | 2043-2050 | |
| 61 | Kit Gomberg | 2 | 2039-2047 | |
| 61 | Pablo Gonzalez | 2 | 2031-2041 | |
| 61 | Ezra Grant# | 2 | 2046-2049 | |
| 61 | Colby Graves# | 2 | 2047-2050 | |
| 61 | Paul Grigg# | 2 | 2045-2050 | |
| 61 | Edwin Guerrero | 2 | 2033-2048 | |
| 61 | Tony Gustafson# | 2 | 2045-2050 | |
| 61 | Logan Hamlin | 2 | 2036-2049 | |
| 61 | Jacob Harris | 2 | 2042-2045 | |
| 61 | John Hazen# | 2 | 2050-2050 | |
| 61 | Jeff Hickam# | 2 | 2044-2050 | |
| 61 | Paul Iglesias | 2 | 2038-2048 | |
| 61 | Ché Jemison# | 2 | 2041-2050 |
