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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Greg Woolery# | 4 | 2043-2045 | |
| 2 | Cody Clayton | 3 | 2030-2031 | |
| 2 | Josh Curran | 3 | 2046-2048 | |
| 2 | Danny Gregory# | 3 | 2057-2060 | |
| 2 | Matt Jenkins | 3 | 2041-2043 | |
| 2 | Chris Jones | 3 | 2039-2041 | |
| 2 | Bill McLean# | 3 | 2049-2052 | |
| 2 | Felix Ruiz | 3 | 2036-2038 | |
| 2 | Chris Sanchez | 3 | 2030-2031 | |
| 2 | Max Van Meter | 3 | 2049-2052 | |
| 11 | Pat Boch# | 2 | 2048-2051 | |
| 11 | Steve Brignola# | 2 | 2057-2060 | |
| 11 | Justin Brown# | 2 | 2049-2052 | |
| 11 | Brad Cearley# | 2 | 2053-2055 | |
| 11 | Tony Colon | 2 | 2035-2037 | |
| 11 | Ricky Desoto | 2 | 2036-2038 | |
| 11 | Ron Dorley# | 2 | 2057-2060 | |
| 11 | Pierre Dumont | 2 | 2040-2041 | |
| 11 | Kevin Felson# | 2 | 2057-2059 | |
| 11 | Steve Fender# | 2 | 2057-2059 | |
| 11 | Elias Gallegos# | 2 | 2056-2059 | |
| 11 | Perry Gamble# | 2 | 2050-2053 | |
| 11 | Sam Godfrey# | 2 | 2059-2060 | |
| 11 | Blake Gottshall# | 2 | 2053-2055 | |
| 11 | Ray Goulding# | 2 | 2058-2060 | |
| 11 | Devin Gramlich | 2 | 2044-2046 | |
| 11 | Chris Hampton# | 2 | 2054-2057 | |
| 11 | Karl Harrison# | 2 | 2053-2056 | |
| 11 | Seiichiro Hirayama | 2 | 2037-2039 | |
| 11 | Tom House# | 2 | 2052-2054 | |
| 11 | Ethan Howell# | 2 | 2053-2056 | |
| 11 | Ted Igo | 2 | 2038-2039 | |
| 11 | Jim Joseph | 2 | 2036-2038 | |
| 11 | Jeff LaMoureaux | 2 | 2034-2036 | |
| 11 | J.P. Larson# | 2 | 2054-2057 | |
| 11 | Jesse Lindsley# | 2 | 2045-2047 | |
| 11 | Juan Luna | 2 | 2034-2036 | |
| 11 | Chris Maloney# | 2 | 2058-2060 | |
| 11 | John McLean# | 2 | 2056-2059 | |
| 11 | Joe Moran | 2 | 2044-2045 | |
| 11 | Marquis Oates | 2 | 2039-2041 | |
| 11 | Ted Osterberg | 2 | 2042-2044 | |
| 11 | Ralph Petsche# | 2 | 2056-2059 | |
| 11 | Gary Queen# | 2 | 2049-2051 | |
| 11 | Carlos Sanchez# | 2 | 2049-2052 | |
| 11 | Phil Schoenberg | 2 | 2045-2047 | |
| 11 | J.T. Shaw | 2 | 2034-2036 | |
| 11 | Chris Tappan# | 2 | 2048-2051 | |
| 11 | Mike Thompson | 2 | 2034-2036 | |
| 11 | Steve Tilley# | 2 | 2054-2057 | |
| 11 | Jim Turner# | 2 | 2052-2054 | |
| 11 | Spencer Waugh# | 2 | 2054-2057 | |
| 11 | Alan Wienczkowski | 2 | 2037-2040 | |
| 11 | Jaden Winfrey | 2 | 2035-2035 | |
| 55 | Erik Adams | 1 | 2043-2044 | |
| 55 | Gene Aikman# | 1 | 2058-2060 | |
| 55 | Norm Anglin# | 1 | 2049-2051 | |
| 55 | Sean Austin | 1 | 2035-2038 | |
| 55 | Craig Bare | 1 | 2042-2045 | |
| 55 | Mike Batten# | 1 | 2054-2057 | |
| 55 | Chad Baumann | 1 | 2040-2042 | |
| 55 | Mike Beale# | 1 | 2051-2054 | |
| 55 | Noel Belcher# | 1 | 2043-2046 | |
| 55 | Chris Bellan | 1 | 2043-2045 | |
| 55 | Paul Beloin | 1 | 2034-2034 | |
| 55 | Chris Benn# | 1 | 2049-2051 | |
| 55 | Adam Boeckner# | 1 | 2060-2060 | |
| 55 | Zach Boggan | 1 | 2039-2042 | |
| 55 | Henry Bonnar | 1 | 2037-2038 | |
| 55 | Steve Brady | 1 | 2042-2044 | |
| 55 | Caleb Brock# | 1 | 2059-2060 | |
| 55 | Corey Brunjes# | 1 | 2049-2052 | |
| 55 | Zach Buchanan# | 1 | 2049-2051 | |
| 55 | Mike Bugg | 1 | 2037-2039 | |
| 55 | Tim Burke | 1 | 2040-2043 | |
| 55 | Nolan Burton | 1 | 2049-2052 | |
| 55 | Mark Cantwell | 1 | 2039-2041 | |
| 55 | Nick Carl# | 1 | 2056-2059 | |
| 55 | Steve Carlson# | 1 | 2050-2053 | |
| 55 | Joe Caudell# | 1 | 2060-2060 | |
| 55 | David Chappell# | 1 | 2056-2059 | |
| 55 | Albert Christensen | 1 | 2045-2047 | |
| 55 | Bob Clark | 1 | 2045-2047 | |
| 55 | Tim Connel# | 1 | 2058-2060 | |
| 55 | Shane Conner# | 1 | 2057-2059 | |
| 55 | Nate Cory# | 1 | 2053-2056 | |
| 55 | Victor Crawford# | 1 | 2057-2060 | |
| 55 | Scott Dagley# | 1 | 2042-2044 | |
| 55 | Sean Davis# | 1 | 2059-2060 | |
| 55 | Steve Dean | 1 | 2044-2046 | |
| 55 | Sam Del Grosso# | 1 | 2053-2055 | |
| 55 | Nick Derr# | 1 | 2049-2051 | |
| 55 | Sean Diehl | 1 | 2048-2051 | |
| 55 | David Doss# | 1 | 2054-2057 | |
| 55 | Kevin Drell# | 1 | 2053-2055 | |
| 55 | Ryan Drumm | 1 | 2046-2048 | |
| 55 | Bryant Duff | 1 | 2040-2043 | |
| 55 | Phil Ebert | 1 | 2034-2037 | |
| 55 | Scott Eiken# | 1 | 2052-2055 | |
| 55 | Juan Estrada# | 1 | 2053-2055 |
