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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Juan Gonzáles# | 5 | 2042-2045 | |
| 1 | John Pitts | 5 | 2036-2039 | |
| 3 | Pete Brooks# | 4 | 2041-2044 | |
| 3 | Robbie Kenney# | 4 | 2046-2049 | |
| 3 | Jeff Riddle | 4 | 2029-2030 | |
| 6 | Jesús Arredondo# | 3 | 2049-2049 | |
| 6 | Sloan Banks# | 3 | 2038-2041 | |
| 6 | Pat Christian | 3 | 2035-2037 | |
| 6 | Octávio Colón# | 3 | 2043-2045 | |
| 6 | Luis Díaz# | 3 | 2046-2046 | |
| 6 | Bill Evans# | 3 | 2045-2048 | |
| 6 | Eric Frank | 3 | 2035-2035 | |
| 6 | Craig Hoover# | 3 | 2032-2034 | |
| 6 | Steve Johnson# | 3 | 2038-2041 | |
| 6 | Jason McNeal# | 3 | 2048-2049 | |
| 6 | Carl Morgan# | 3 | 2038-2041 | |
| 6 | Kenneth Noble# | 3 | 2031-2033 | |
| 6 | Reginald Rincón# | 3 | 2040-2042 | |
| 6 | Zach Robbins# | 3 | 2045-2048 | |
| 6 | Paul Russell# | 3 | 2049-2049 | |
| 6 | Justin Smith# | 3 | 2036-2039 | |
| 6 | Ronnie Wilson | 3 | 2038-2041 | |
| 23 | Jay Alejandro# | 2 | 2046-2049 | |
| 23 | Ed Andrews | 2 | 2034-2035 | |
| 23 | Aaron Bentinck# | 2 | 2043-2045 | |
| 23 | Michael Brown# | 2 | 2042-2045 | |
| 23 | Zachary Burke# | 2 | 2045-2048 | |
| 23 | Darrel Burns# | 2 | 2037-2040 | |
| 23 | Herman Carey# | 2 | 2046-2049 | |
| 23 | Chris Chadwell# | 2 | 2038-2041 | |
| 23 | Al Combs# | 2 | 2043-2045 | |
| 23 | R.A. Cotton | 2 | 2031-2033 | |
| 23 | Dave Covington# | 2 | 2043-2045 | |
| 23 | Mike Crawford# | 2 | 2042-2045 | |
| 23 | Roger Davis# | 2 | 2036-2039 | |
| 23 | John England | 2 | 2033-2035 | |
| 23 | Harry Findlay# | 2 | 2041-2044 | |
| 23 | William Fitzpatrick# | 2 | 2042-2045 | |
| 23 | Joe Franklin | 2 | 2033-2035 | |
| 23 | Derek Frazier | 2 | 2036-2036 | |
| 23 | Leonardo García# | 2 | 2036-2039 | |
| 23 | Carlos González# | 2 | 2033-2035 | |
| 23 | Tyler Hanna# | 2 | 2039-2040 | |
| 23 | Marvin Harrison | 2 | 2030-2032 | |
| 23 | Steffen Higgins# | 2 | 2045-2048 | |
| 23 | Terrence Jarville# | 2 | 2039-2042 | |
| 23 | Pedro Jiménez# | 2 | 2048-2049 | |
| 23 | Brian Jones# | 2 | 2038-2041 | |
| 23 | John King# | 2 | 2045-2048 | |
| 23 | Jerry Martínez# | 2 | 2043-2045 | |
| 23 | Mike McManus# | 2 | 2042-2045 | |
| 23 | Quentin Miller# | 2 | 2043-2045 | |
| 23 | Eric Mitchell# | 2 | 2043-2045 | |
| 23 | Leland Moore# | 2 | 2044-2047 | |
| 23 | Héctor Moreno# | 2 | 2047-2049 | |
| 23 | Michihiro Naito# | 2 | 2046-2049 | |
| 23 | Tomás Nieves | 2 | 2032-2034 | |
| 23 | Scott Niles# | 2 | 2046-2048 | |
| 23 | Marc O'Dwyer | 2 | 2027-2029 | |
| 23 | Quinn Peck# | 2 | 2039-2041 | |
| 23 | Chris Phillips# | 2 | 2041-2044 | |
| 23 | Bill Regush# | 2 | 2046-2046 | |
| 23 | Bartolo Rodríguez# | 2 | 2047-2047 | |
| 23 | Nicholas Ryding# | 2 | 2046-2049 | |
| 23 | Fred Sharp# | 2 | 2038-2041 | |
| 23 | Howard Smith# | 2 | 2043-2045 | |
| 23 | Tom Spruill# | 2 | 2043-2045 | |
| 23 | Fa-hsien Thum# | 2 | 2038-2039 | |
| 23 | José Vega# | 2 | 2046-2049 | |
| 23 | John Ward# | 2 | 2038-2041 | |
| 23 | Joey Waters# | 2 | 2046-2049 | |
| 23 | Ed Weaver# | 2 | 2040-2041 | |
| 23 | Samuel Wesman# | 2 | 2043-2045 | |
| 23 | Ralph Wilhelm# | 2 | 2036-2039 | |
| 75 | Roberto Aguirre# | 1 | 2049-2049 | |
| 75 | Yurdakul Al-Jurjâni# | 1 | 2046-2049 | |
| 75 | Dan Allen# | 1 | 2041-2044 | |
| 75 | Ray Anderson | 1 | 2029-2031 | |
| 75 | Fernando Arrojo# | 1 | 2033-2035 | |
| 75 | Mike Bacon# | 1 | 2039-2042 | |
| 75 | Eddie Baker# | 1 | 2038-2041 | |
| 75 | Geoff Bannatyne# | 1 | 2038-2041 | |
| 75 | Jason Barnes# | 1 | 2042-2045 | |
| 75 | Bob Barrett# | 1 | 2046-2047 | |
| 75 | Ira Bass# | 1 | 2042-2045 | |
| 75 | Tim Baxter# | 1 | 2039-2040 | |
| 75 | Christian Bouton# | 1 | 2036-2039 | |
| 75 | Ed Bowden | 1 | 2030-2032 | |
| 75 | Greg Bowles# | 1 | 2041-2044 | |
| 75 | Dave Bradshaw# | 1 | 2038-2041 | |
| 75 | Cody Brady# | 1 | 2048-2049 | |
| 75 | Guillermo Cabrera | 1 | 2032-2034 | |
| 75 | Craig Carter# | 1 | 2040-2043 | |
| 75 | Hollis Carter# | 1 | 2043-2045 | |
| 75 | Jonah Cline# | 1 | 2046-2046 | |
| 75 | António Cobellén# | 1 | 2048-2049 | |
| 75 | Carl Collins# | 1 | 2036-2038 | |
| 75 | John Comer# | 1 | 2048-2049 | |
| 75 | Larry Cook# | 1 | 2042-2045 | |
| 75 | Mike Cowan# | 1 | 2039-2042 |
