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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 | Christy Mathewson | .1905 | 1906 | |
| 4 | Frank Smith | .2063 | 1908 | |
| 5 | Harry Krause | .2069 | 1909 | |
| 6 | Mordecai Brown | .2206 | 1909 | |
| 7 | Al Demaree# | .2222 | 1916 | |
| 8 | George Mullin | .2264 | 1907 | |
| 9 | Addie Joss | .2319 | 1905 | |
| 10 | Ferdie Schupp# | .2344 | 1916 | |
| 10 | Eddie Plank# | .2344 | 1908 | |
| 12 | Jesse Tannehill | .2381 | 1903 | |
| 13 | Kid Nichols* | .2394 | 1892 | |
| 14 | Bill Donovan# | .2419 | 1907 | |
| 15 | Cy Young* | .2500 | 1901 | |
| 16 | Orval Overall | .2542 | 1910 | |
| 16 | Joe Williams# | .2542 | 1910 | |
| 18 | Joe Wood# | .2609 | 1915 | |
| 19 | Charles Bender# | .2639 | 1903 | |
| 20 | Babe Adams# | .2656 | 1913 | |
| 21 | Cy Young* | .2710 | 1892 | |
| 22 | Addie Joss | .2742 | 1906 | |
| 23 | Dutch Leonard# | .2759 | 1914 | |
| 24 | Christy Mathewson | .2769 | 1904 | |
| 25 | Babe Adams# | .2879 | 1914 | |
| 26 | Russ Ford | .2903 | 1910 | |
| 27 | Charles Bender# | .2907 | 1912 | |
| 28 | Jack Chesbro | .2955 | 1907 | |
| 29 | Charles Bender# | .3000 | 1908 | |
| 30 | Dutch Leonard# | .3059 | 1916 | |
| 31 | Jesse Tannehill | .3077 | 1901 | |
| 32 | Jeff Tesreau# | .3134 | 1914 | |
| 33 | Tom Hughes | .3137 | 1909 | |
| 34 | George McQuillan# | .3194 | 1908 | |
| 35 | Orval Overall | .3226 | 1909 | |
| 35 | Weldon Henley | .3226 | 1903 | |
| 37 | Rube Marquard# | .3281 | 1911 | |
| 37 | Charlie Smith | .3281 | 1907 | |
| 39 | Charles Bender# | .3380 | 1911 | |
| 39 | Babe Ruth# | .3380 | 1916 | |
| 41 | Joe Lake | .3492 | 1910 | |
| 42 | Eddie Plank# | .3514 | 1903 | |
| 43 | Charles Bender# | .3521 | 1913 | |
| 44 | Otto Hess | .3559 | 1906 | |
| 45 | Dutch Leonard# | .3582 | 1915 | |
| 46 | Jeff Tesreau# | .3651 | 1915 | |
| 47 | Vean Gregg# | .3662 | 1911 | |
| 48 | Christy Mathewson | .3676 | 1911 | |
| 49 | Rube Waddell | .3684 | 1901 | |
| 50 | Doc White | .3710 | 1906 | |
| 51 | Claude Hendrix# | .3750 | 1912 | |
| 52 | Rube Waddell | .3810 | 1908 | |
| 53 | George McConnell | .4000 | 1913 | |
| 54 | Red Ames# | .4068 | 1911 | |
| 55 | Rube Waddell | .4143 | 1902 | |
| 56 | Red Ames# | .4167 | 1905 | |
| 56 | Bill Bernhard | .4167 | 1906 | |
| 58 | Mordecai Brown | .4219 | 1910 | |
| 59 | Mordecai Brown | .4227 | 1907 | |
| 60 | Charles Bender# | .4262 | 1909 | |
| 61 | Jack Pfiester | .4265 | 1907 | |
| 62 | George Winter | .4479 | 1901 | |
| 63 | Rube Marquard# | .4590 | 1914 | |
| 64 | Vean Gregg# | .4769 | 1913 |
