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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Sherry Smith | .1700 | 1911-1927 | |
| 2 | Eddie Plank* | .1859 | 1901-1917 | |
| 3 | Lefty Tyler | .1864 | 1910-1924 | |
| 4 | Ernie Shore | .1935 | 1912-1920 | |
| 5 | Satchel Paige# | .1953 | 1933-1940 | |
| 6 | Orval Overall | .1979 | 1905-1913 | |
| 7 | Lady Baldwin | .2013 | 1884-1890 | |
| 8 | Ed Reulbach | .2034 | 1905-1917 | |
| 9 | Deacon Phillippe | .2041 | 1899-1911 | |
| 10 | Christy Mathewson* | .2069 | 1900-1916 | |
| 11 | Babe Ruth | .2095 | 1914-1937 | |
| 12 | Chief Bender* | .2208 | 1903-1917 | |
| 13 | George Mullin | .2212 | 1902-1915 | |
| 14 | Tim Keefe | .2237 | 1880-1893 | |
| 15 | Mordecai Brown* | .2252 | 1903-1916 | |
| 16 | Bill Dinneen | .2302 | 1898-1909 | |
| 17 | Jack Coombs | .2356 | 1906-1920 | |
| 18 | Bob Shawkey | .2366 | 1913-1928 | |
| 19 | Pete Conway | .2385 | 1885-1889 | |
| 20 | Bill Donovan | .2404 | 1898-1918 | |
| 21 | Silver King | .2414 | 1886-1897 | |
| 22 | Eddie Cicotte* | .2428 | 1905-1920 | |
| 23 | Jim McCormick | .2500 | 1878-1887 | |
| 24 | Ed Crane | .2536 | 1884-1893 | |
| 25 | Cy Young* | .2582 | 1890-1911 | |
| 26 | Willie Foster | .2606 | 1931-1939 | |
| 27 | Jimmy Ring | .2609 | 1917-1930 | |
| 28 | John Clarkson | .2617 | 1882-1894 | |
| 29 | Jeff Tesreau | .2640 | 1912-1918 | |
| 30 | Pretzels Getzien | .2723 | 1884-1892 | |
| 31 | Rube Marquard* | .2832 | 1908-1924 | |
| 32 | Jack Pfiester | .2836 | 1903-1911 | |
| 33 | Tom Lovett | .2848 | 1885-1894 | |
| 34 | Bob Caruthers | .2865 | 1884-1892 | |
| 35 | Mort Cooper# | .2885 | 1938-1941 | |
| 36 | Stan Coveleski | .2968 | 1912-1927 | |
| 37 | Dave Foutz | .2981 | 1884-1896 | |
| 38 | Adonis Terry | .3023 | 1884-1897 | |
| 39 | Jesse Haines | .3034 | 1918-1936 | |
| 40 | Jack Quinn | .3061 | 1909-1928 | |
| 41 | Red Faber* | .3186 | 1914-1931 | |
| 42 | Lefty Grove# | .3279 | 1925-1941 | |
| 43 | Ice Box Chamberlin | .3315 | 1886-1896 | |
| 44 | Eppa Rixey* | .3333 | 1912-1935 | |
| 45 | Bill Lohrman# | .3564 | 1935-1941 | |
| 46 | Carl Hubbell# | .3618 | 1928-1941 | |
| 47 | Bobo Newsom# | .3718 | 1929-1941 | |
| 48 | Dutch Leonard | .3734 | 1913-1927 | |
| 49 | Rube Walberg | .3764 | 1923-1936 | |
| 50 | Sad Sam Jones | .3895 | 1914-1936 | |
| 51 | Waite Hoyt | .4043 | 1918-1940 | |
| 52 | Bill Hallahan | .4169 | 1926-1938 | |
| 53 | George Earnshaw | .4235 | 1928-1937 | |
| 54 | Burleigh Grimes | .4331 | 1916-1932 | |
| 55 | Roy Parmelee# | .4407 | 1930-1940 | |
| 56 | Ted Lyons# | .4419 | 1923-1941 | |
| 57 | Dizzy Dean# | .4444 | 1930-1941 | |
| 58 | Paul Derringer# | .4469 | 1931-1941 | |
| 59 | Bill Walker# | .4548 | 1927-1938 | |
| 60 | Art Nehf | .4555 | 1915-1930 | |
| 61 | Ted Trent | .4703 | 1937-1939 | |
| 62 | Hal Schumacher# | .5363 | 1931-1941 |
