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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 | George Mullin | .2264 | 1907 | |
| 8 | Addie Joss | .2319 | 1905 | |
| 9 | Eddie Plank# | .2344 | 1908 | |
| 10 | Jesse Tannehill | .2381 | 1903 | |
| 11 | Kid Nichols* | .2394 | 1892 | |
| 12 | Bill Donovan# | .2419 | 1907 | |
| 13 | Cy Young | .2500 | 1901 | |
| 14 | Joe Williams# | .2542 | 1910 | |
| 14 | Orval Overall | .2542 | 1910 | |
| 16 | Joe Wood# | .2609 | 1915 | |
| 17 | Charles Bender# | .2639 | 1903 | |
| 18 | Babe Adams# | .2656 | 1913 | |
| 19 | Cy Young | .2710 | 1892 | |
| 20 | Addie Joss | .2742 | 1906 | |
| 21 | Dutch Leonard# | .2759 | 1914 | |
| 22 | Christy Mathewson# | .2769 | 1904 | |
| 23 | Babe Adams# | .2879 | 1914 | |
| 24 | Russ Ford | .2903 | 1910 | |
| 25 | Charles Bender# | .2907 | 1912 | |
| 26 | Jack Chesbro | .2955 | 1907 | |
| 27 | Charles Bender# | .3000 | 1908 | |
| 28 | Jesse Tannehill | .3077 | 1901 | |
| 29 | Jeff Tesreau# | .3134 | 1914 | |
| 30 | Tom Hughes | .3137 | 1909 | |
| 31 | George McQuillan# | .3194 | 1908 | |
| 32 | Orval Overall | .3226 | 1909 | |
| 32 | Weldon Henley | .3226 | 1903 | |
| 34 | Rube Marquard# | .3281 | 1911 | |
| 34 | Charlie Smith | .3281 | 1907 | |
| 36 | Charles Bender# | .3380 | 1911 | |
| 37 | Joe Lake | .3492 | 1910 | |
| 38 | Eddie Plank# | .3514 | 1903 | |
| 39 | Charles Bender# | .3521 | 1913 | |
| 40 | Otto Hess | .3559 | 1906 | |
| 41 | Dutch Leonard# | .3582 | 1915 | |
| 42 | Jeff Tesreau# | .3651 | 1915 | |
| 43 | Vean Gregg# | .3662 | 1911 | |
| 44 | Christy Mathewson# | .3676 | 1911 | |
| 45 | Rube Waddell | .3684 | 1901 | |
| 46 | Doc White | .3710 | 1906 | |
| 47 | Claude Hendrix# | .3750 | 1912 | |
| 48 | Rube Waddell | .3810 | 1908 | |
| 49 | George McConnell# | .4000 | 1913 | |
| 50 | Red Ames# | .4068 | 1911 | |
| 51 | Rube Waddell | .4143 | 1902 | |
| 52 | Red Ames# | .4167 | 1905 | |
| 52 | Bill Bernhard | .4167 | 1906 | |
| 54 | Mordecai Brown# | .4219 | 1910 | |
| 55 | Mordecai Brown# | .4227 | 1907 | |
| 56 | Charles Bender# | .4262 | 1909 | |
| 57 | Jack Pfiester | .4265 | 1907 | |
| 58 | George Winter | .4479 | 1901 | |
| 59 | Rube Marquard# | .4590 | 1914 | |
| 60 | Vean Gregg# | .4769 | 1913 |
