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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Matt Gilman* | .744 | 2051-2071 | |
| 2 | Evan Parker* | .740 | 2070-2086 | |
| 3 | Javier Covarrubias* | .731 | 2061-2077 | |
| 4 | Alberto Cigarroa | .723 | 2056-2070 | |
| 5 | Spud Chandler | .717 | 1937-1947 | |
| 6 | Marc Braswell | .716 | 2062-2073 | |
| 7 | Sean Lebron | .709 | 2061-2073 | |
| 8 | Travis Austad | .706 | 2079-2089 | |
| 9 | Juan Fernandez* | .703 | 2053-2066 | |
| 10 | Fred Cloninger* | .700 | 2033-2044 | |
| 11 | Brian Casey* | .698 | 2048-2061 | |
| 12 | Jose Alvarez | .697 | 2041-2053 | |
| 13 | Jose Cardenas | .696 | 2073-2084 | |
| 14 | Matt Whisler* | .690 | 2042-2056 | |
| 14 | Whitey Ford* | .690 | 1950-1967 | |
| 16 | Chris Flores | .688 | 2060-2071 | |
| 17 | Corey Winer | .687 | 2075-2088 | |
| 17 | Noel Murch* | .687 | 2039-2057 | |
| 17 | Pedro Martinez* | .687 | 1992-2009 | |
| 20 | Don Gullett | .686 | 1970-1978 | |
| 21 | Deivi Garcia* | .682 | 2020-2035 | |
| 22 | Billy Cornette | .681 | 2084-2091 | |
| 22 | Nick Cerqueira | .681 | 2055-2066 | |
| 22 | Eric Beattie# | .681 | 2088-2098 | |
| 22 | Manny Cruz* | .681 | 2027-2043 | |
| 22 | Matt Patras# | .681 | 2092-2098 | |
| 27 | Lefty Grove* | .680 | 1925-1941 | |
| 27 | Roberto Arceo* | .680 | 2033-2049 | |
| 29 | Rico Rolon | .678 | 2040-2056 | |
| 29 | Salvador Calderon | .678 | 2044-2055 | |
| 31 | Jimmy Ward | .677 | 2048-2059 | |
| 32 | Brian Clouse | .674 | 2047-2060 | |
| 32 | Chris Hafer# | .674 | 2091-2098 | |
| 32 | Akeel Morris | .674 | 2015-2030 | |
| 35 | Max Fried* | .673 | 2017-2030 | |
| 35 | Alex Batista* | .673 | 2058-2073 | |
| 35 | Larry Corcoran | .673 | 1880-1886 | |
| 35 | Fernando Cervantes | .673 | 2069-2084 | |
| 39 | Mike Rostkowski | .672 | 2045-2061 | |
| 39 | Joe Wood | .672 | 1908-1922 | |
| 39 | Vince Evers | .672 | 2076-2091 | |
| 42 | Babe Ruth* | .671 | 1914-1935 | |
| 43 | Luis Ibarra | .670 | 2054-2064 | |
| 43 | Kyle Milner | .670 | 2084-2096 | |
| 45 | Brian LaHale | .669 | 2063-2075 | |
| 45 | Mario Segura* | .669 | 2060-2080 | |
| 45 | Sean Pester | .669 | 2042-2052 | |
| 48 | Vic Raschi | .667 | 1946-1955 | |
| 48 | Tony Ulloa | .667 | 2064-2076 | |
| 50 | Josh Lowe | .666 | 2033-2047 | |
| 51 | Jeremy LeVan | .665 | 2053-2064 | |
| 51 | Christy Mathewson* | .665 | 1900-1916 | |
| 53 | Nate Howe | .664 | 2063-2077 | |
| 54 | David Acosta | .663 | 2058-2072 | |
| 54 | Logan Lowe* | .663 | 2062-2079 | |
| 56 | Ben Hunter | .662 | 2083-2095 | |
| 57 | Dan Howery | .660 | 2034-2051 | |
| 57 | Sam Leever | .660 | 1898-1910 | |
| 59 | Cory Jann | .659 | 2068-2080 | |
| 59 | Roy Halladay* | .659 | 1998-2013 | |
| 59 | Gabriel Simmons* | .659 | 2026-2043 | |
| 62 | Roger Clemens | .658 | 1984-2007 | |
| 62 | Steve Hawkins | .658 | 2030-2040 | |
| 64 | Sal Maglie | .657 | 1945-1958 | |
| 65 | Sandy Koufax* | .655 | 1955-1966 | |
| 66 | Johnny Allen | .654 | 1932-1944 | |
| 67 | Tony Watson | .653 | 2011-2026 | |
| 67 | Danny Fonseca | .653 | 2028-2041 | |
| 69 | Chief Bender* | .652 | 1903-1925 | |
| 69 | Mordecai Brown* | .652 | 1903-1916 | |
| 71 | Ron Guidry | .651 | 1975-1988 | |
| 71 | Tony Soto# | .651 | 2088-2098 | |
| 71 | Jose Rubio* | .651 | 2060-2079 | |
| 71 | Joe McGinnity* | .651 | 1900-1908 | |
| 71 | Ricardo Rivera | .651 | 2023-2044 | |
| 76 | Leo Monrreal* | .650 | 2031-2044 | |
| 76 | Robert Bartos# | .650 | 2090-2098 | |
| 76 | Enrique Perez | .650 | 2020-2037 | |
| 79 | Lefty Gomez* | .649 | 1930-1943 | |
| 80 | Roger Diaz# | .648 | 2090-2098 | |
| 80 | John Clarkson* | .648 | 1882-1894 | |
| 80 | Ricardo Raya | .648 | 2030-2045 | |
| 83 | Sean Ouellette | .647 | 2038-2052 | |
| 84 | Victor Estrada | .646 | 2056-2071 | |
| 84 | Deacon Phillippe | .646 | 1900-1911 | |
| 84 | Randy Johnson* | .646 | 1988-2009 | |
| 84 | Bob Antoine | .646 | 2040-2047 | |
| 84 | Adam Laskey | .646 | 2024-2034 | |
| 84 | Jaylen Watts* | .646 | 2067-2086 | |
| 84 | Mike Coles | .646 | 2058-2072 | |
| 91 | Josh Jackson | .645 | 2061-2074 | |
| 91 | Gene Fisher | .645 | 2036-2050 | |
| 91 | Jose Ulibarri | .645 | 2071-2083 | |
| 91 | Bryce Robinson | .645 | 2057-2071 | |
| 95 | Austin Priester | .644 | 2031-2045 | |
| 95 | Dizzy Dean* | .644 | 1930-1947 | |
| 97 | Gabe Fay* | .643 | 2069-2089 | |
| 97 | Dane Borkholder | .643 | 2075-2087 | |
| 99 | Pete Alexander* | .642 | 1911-1930 | |
| 99 | Jake Reed | .642 | 2025-2041 |
