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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Postseason Career Leaderboard |
|---|---|---|---|---|
| 1 | Rube Waddell* | .1639 | 1903 | |
| 2 | Hooks Wiltse | .1803 | 1906 | |
| 3 | Bill Doak | .1864 | 1920 | |
| 4 | Christy Mathewson* | .1905 | 1906 | |
| 5 | Connie Marrero | .1935 | 1952 | |
| 5 | Jeff Pfeffer | .1935 | 1917 | |
| 7 | Frank Smith | .2063 | 1908 | |
| 8 | Harry Krause | .2069 | 1909 | |
| 9 | Satchel Paige | .2083 | 1948 | |
| 10 | Tiny Bonham | .2097 | 1941 | |
| 11 | Red Faber | .2105 | 1920 | |
| 12 | Mordecai Brown* | .2206 | 1909 | |
| 13 | Al Demaree | .2222 | 1916 | |
| 14 | George Mullin | .2264 | 1907 | |
| 15 | Babe Adams* | .2295 | 1922 | |
| 16 | Van Mungo# | .2308 | 1952 | |
| 17 | Addie Joss* | .2319 | 1905 | |
| 18 | Bill Bevens# | .2333 | 1954 | |
| 19 | Ferdie Schupp | .2344 | 1916 | |
| 19 | Eddie Plank* | .2344 | 1908 | |
| 21 | Jesse Tannehill | .2381 | 1903 | |
| 22 | Kid Nichols* | .2394 | 1892 | |
| 23 | Max Lanier | .2407 | 1942 | |
| 24 | Bill Donovan | .2419 | 1907 | |
| 25 | Spud Chandler | .2453 | 1949 | |
| 26 | Lefty Gomez | .2500 | 1939 | |
| 26 | Cy Young* | .2500 | 1901 | |
| 26 | Hal Schumacher | .2500 | 1934 | |
| 26 | Ed Brandt | .2500 | 1932 | |
| 30 | Joe Williams* | .2542 | 1910 | |
| 30 | Orval Overall | .2542 | 1910 | |
| 32 | Joe Wood | .2609 | 1915 | |
| 33 | Charles Bender* | .2639 | 1903 | |
| 34 | Babe Adams* | .2656 | 1913 | |
| 35 | Cy Young* | .2710 | 1892 | |
| 36 | Tiny Bonham | .2742 | 1942 | |
| 36 | Addie Joss* | .2742 | 1906 | |
| 38 | Jack Quinn | .2747 | 1918 | |
| 39 | Dutch Leonard | .2759 | 1914 | |
| 40 | Christy Mathewson* | .2769 | 1904 | |
| 41 | Babe Adams* | .2879 | 1914 | |
| 42 | Hilton Smith | .2881 | 1932 | |
| 43 | Russ Ford | .2903 | 1910 | |
| 44 | Charles Bender* | .2907 | 1912 | |
| 45 | Jack Chesbro | .2955 | 1907 | |
| 46 | Hal Schumacher | .2963 | 1936 | |
| 46 | Johnny Allen | .2963 | 1940 | |
| 48 | Johnny Allen | .2982 | 1939 | |
| 48 | Bill Hallahan | .2982 | 1935 | |
| 50 | Charles Bender* | .3000 | 1908 | |
| 51 | Jakie May | .3026 | 1928 | |
| 52 | Jack Quinn | .3051 | 1921 | |
| 53 | Dutch Leonard | .3059 | 1916 | |
| 54 | Jesse Tannehill | .3077 | 1901 | |
| 55 | Jeff Tesreau | .3134 | 1914 | |
| 56 | Tom Hughes | .3137 | 1909 | |
| 57 | Webster McDonald | .3143 | 1930 | |
| 58 | Gentry Jessup# | .3188 | 1950 | |
| 58 | Carl Hubbell* | .3188 | 1929 | |
| 60 | George McQuillan | .3194 | 1908 | |
| 61 | Eddie Cicotte* | .3214 | 1922 | |
| 62 | Weldon Henley | .3226 | 1903 | |
| 62 | Orval Overall | .3226 | 1909 | |
| 64 | Rube Marquard | .3281 | 1911 | |
| 64 | Charlie Smith | .3281 | 1907 | |
| 66 | Mort Cooper | .3284 | 1942 | |
| 67 | Dutch Leonard | .3333 | 1918 | |
| 67 | Wilbur Cooper | .3333 | 1921 | |
| 67 | Ray Brown | .3333 | 1939 | |
| 70 | Babe Ruth* | .3380 | 1916 | |
| 70 | Charles Bender* | .3380 | 1911 | |
| 72 | Sam Jones | .3387 | 1928 | |
| 72 | Jesse Haines | .3387 | 1928 | |
| 74 | Carl Mays | .3429 | 1918 | |
| 75 | Hal Schumacher | .3492 | 1935 | |
| 75 | Joe Lake | .3492 | 1910 | |
| 77 | Lefty Gomez | .3509 | 1931 | |
| 77 | Barney Morris | .3509 | 1935 | |
| 79 | Eddie Plank* | .3514 | 1903 | |
| 80 | Charles Bender* | .3521 | 1913 | |
| 81 | Jesse Haines | .3548 | 1920 | |
| 82 | Jack Harshman# | .3559 | 1954 | |
| 82 | Otto Hess | .3559 | 1906 | |
| 84 | Dutch Leonard | .3582 | 1915 | |
| 85 | Lefty Grove* | .3607 | 1929 | |
| 86 | Jeff Tesreau | .3651 | 1915 | |
| 87 | Vean Gregg | .3662 | 1911 | |
| 88 | Walter Johnson* | .3667 | 1926 | |
| 89 | Christy Mathewson* | .3676 | 1911 | |
| 90 | Rube Waddell* | .3684 | 1901 | |
| 90 | Ewell Blackwell# | .3684 | 1949 | |
| 92 | Hod Eller | .3710 | 1918 | |
| 92 | Doc White | .3710 | 1906 | |
| 94 | Dick Redding | .3714 | 1917 | |
| 95 | Claude Hendrix | .3750 | 1912 | |
| 96 | Freddie Fitzsimmons | .3770 | 1937 | |
| 97 | Rube Waddell* | .3810 | 1908 | |
| 98 | Ray Fisher | .3824 | 1920 | |
| 99 | Bill Doak | .3827 | 1921 | |
| 100 | Dutch Leonard | .3832 | 1917 |
