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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Dan Brown# | 45 | 2052-2056 | |
| 2 | Billy Robinson | 36 | 2044-2048 | |
| 3 | Riccardo de Dood# | 33 | 2054-2057 | |
| 4 | Kyle Peacock# | 32 | 2055-2059 | |
| 5 | Brady Metro# | 31 | 2057-2060 | |
| 5 | Mike Wynkoop# | 31 | 2056-2060 | |
| 7 | Danny Coyle# | 30 | 2055-2059 | |
| 7 | Jeff King | 30 | 2042-2046 | |
| 7 | J.P. Larson# | 30 | 2057-2060 | |
| 7 | Manny Melgoza# | 30 | 2053-2057 | |
| 7 | Marlon Walton# | 30 | 2058-2060 | |
| 12 | Sam Del Grosso# | 29 | 2055-2059 | |
| 12 | Vince Ellerbee | 29 | 2050-2052 | |
| 14 | Virgile Marletti# | 28 | 2056-2060 | |
| 14 | Jose Ramos# | 28 | 2054-2057 | |
| 16 | Nate Gavin# | 27 | 2058-2060 | |
| 17 | Jamie Feola | 26 | 2047-2050 | |
| 18 | Tom House# | 25 | 2054-2058 | |
| 18 | John Smirnov# | 25 | 2057-2060 | |
| 18 | Josh Wucherer# | 25 | 2056-2059 | |
| 21 | Éric Coulon# | 24 | 2057-2059 | |
| 21 | Adam DeVoe# | 24 | 2055-2058 | |
| 21 | John Farrar# | 24 | 2050-2054 | |
| 21 | Kyle Feinberg# | 24 | 2049-2052 | |
| 21 | Eric Foley# | 24 | 2053-2055 | |
| 21 | Justin Horn | 24 | 2047-2050 | |
| 21 | Jim Kein# | 24 | 2058-2060 | |
| 21 | Jason Murphy# | 24 | 2054-2057 | |
| 21 | Chris Olson# | 24 | 2052-2056 | |
| 21 | Jared Vanderford# | 24 | 2057-2059 | |
| 31 | Lenny Dykstra Jr. | 23 | 2039-2041 | |
| 31 | Mike Olejarz# | 23 | 2055-2057 | |
| 31 | Chad Reid# | 23 | 2055-2056 | |
| 31 | Luis Sosa# | 23 | 2058-2060 | |
| 35 | Gabriel Aguirre | 22 | 2041-2044 | |
| 35 | Jerry Bamberg# | 22 | 2055-2058 | |
| 35 | Gavin Birchall# | 22 | 2056-2058 | |
| 35 | Justin Martin# | 22 | 2058-2060 | |
| 35 | Jerry Pearson# | 22 | 2054-2057 | |
| 35 | Dave Recer# | 22 | 2055-2058 | |
| 35 | Lodewijk van de Wetering | 22 | 2032-2035 | |
| 35 | Mauricio Villegas | 22 | 2044-2047 | |
| 43 | Bill Cavanagh# | 21 | 2056-2060 | |
| 43 | John Haslam# | 21 | 2057-2060 | |
| 43 | Tom Novak# | 21 | 2058-2060 | |
| 43 | Miguel Ortiz | 21 | 2038-2040 | |
| 43 | Abdul Taylor# | 21 | 2057-2060 | |
| 43 | David Thiel | 21 | 2048-2052 | |
| 43 | Dan Wendell | 21 | 2047-2049 | |
| 43 | Matt White | 21 | 2051-2052 | |
| 51 | Rich Hogue# | 20 | 2053-2056 | |
| 51 | Manny Irizarry# | 20 | 2055-2058 | |
| 51 | Kyle King | 20 | 2051-2054 | |
| 51 | John Light# | 20 | 2053-2057 | |
| 51 | Ottaviano Manfredi | 20 | 2051-2052 | |
| 51 | Greg Marshik# | 20 | 2055-2058 | |
| 51 | Maverick McCoy | 20 | 2044-2048 | |
| 51 | Robby Medlin# | 20 | 2054-2058 | |
| 51 | Josh Prosek | 20 | 2052-2056 | |
| 51 | Ernesto Torres# | 20 | 2056-2059 | |
| 61 | Jarrett Allen# | 19 | 2054-2058 | |
| 61 | Hector Bonilla | 19 | 2030-2033 | |
| 61 | Brad Cearley# | 19 | 2055-2059 | |
| 61 | Jason Cochran# | 19 | 2057-2060 | |
| 61 | Dale Koehler | 19 | 2054-2055 | |
| 61 | Mike McMaster | 19 | 2047-2051 | |
| 61 | Dusty Murphy | 19 | 2044-2048 | |
| 61 | David Neeley# | 19 | 2055-2059 | |
| 61 | Juan Orozco# | 19 | 2051-2054 | |
| 61 | Andy Schutt# | 19 | 2057-2059 | |
| 61 | Victor Vicente# | 19 | 2047-2049 | |
| 61 | Elias Zuniga# | 19 | 2047-2049 | |
| 73 | Jordan Berrios | 18 | 2046-2048 | |
| 73 | Mike Diego | 18 | 2050-2051 | |
| 73 | George Ferry | 18 | 2044-2048 | |
| 73 | Cole Filter# | 18 | 2056-2058 | |
| 73 | Juan Macias# | 18 | 2053-2056 | |
| 73 | Matt Meyer# | 18 | 2056-2058 | |
| 73 | Jimmy Welch# | 18 | 2057-2059 | |
| 80 | Monty Brewster# | 17 | 2053-2057 | |
| 80 | Pedro Cerna | 17 | 2032-2036 | |
| 80 | Andres Chavez# | 17 | 2054-2056 | |
| 80 | Ryan Davis# | 17 | 2054-2057 | |
| 80 | Alex Estrada# | 17 | 2059-2060 | |
| 80 | Akira Fukuda# | 17 | 2054-2057 | |
| 80 | Alpha Kennison# | 17 | 2053-2055 | |
| 80 | Tony Lopez# | 17 | 2054-2057 | |
| 80 | Josh Macro# | 17 | 2054-2058 | |
| 80 | Mike Statzer# | 17 | 2047-2050 | |
| 80 | Nick Swann# | 17 | 2058-2060 | |
| 80 | Earl Tisdale | 17 | 2055-2058 | |
| 80 | Greg Woolery# | 17 | 2045-2049 | |
| 93 | Caleb Broussard# | 16 | 2057-2058 | |
| 93 | Jose Calderon# | 16 | 2052-2053 | |
| 93 | Leo Campa | 16 | 2045-2048 | |
| 93 | Mark Cowen# | 16 | 2049-2053 | |
| 93 | Zion Dennison# | 16 | 2055-2057 | |
| 93 | Karl Harrison# | 16 | 2056-2057 | |
| 93 | Lance Kaeser# | 16 | 2057-2058 | |
| 93 | Fidel Lechuga | 16 | 2050-2051 |
