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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | OSLG | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Addie Joss | .2519 | 1902-1910 | |
| 2 | Jesse Tannehill | .2751 | 1894-1910 | |
| 3 | Babe Adams# | .2769 | 1906-1915 | |
| 4 | Orval Overall | .2823 | 1905-1913 | |
| 5 | Eddie Plank# | .2971 | 1901-1915 | |
| 6 | Cy Young | .2990 | 1890-1911 | |
| 7 | Dutch Leonard# | .3200 | 1913-1915 | |
| 8 | Jeff Tesreau# | .3235 | 1912-1915 | |
| 9 | Charles Bender# | .3248 | 1903-1915 | |
| 10 | Christy Mathewson# | .3502 | 1900-1915 | |
| 11 | Rube Waddell | .3528 | 1897-1910 | |
| 12 | Deacon Phillippe | .3556 | 1899-1911 | |
| 13 | Mordecai Brown# | .3624 | 1903-1915 | |
| 14 | Red Ames# | .3763 | 1903-1915 | |
| 15 | Joe Wood# | .3955 | 1908-1915 | |
| 16 | Otto Hess | .3966 | 1902-1914 | |
| 17 | Bill Bernhard | .4173 | 1899-1907 | |
| 18 | Rube Marquard# | .4267 | 1908-1915 | |
| 19 | Jack Pfiester | .4397 | 1904-1911 | |
| 20 | Vean Gregg# | .4574 | 1911-1915 |
