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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | WPCT | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Babe Adams# | 1.000 | 1906-1916 | |
| 2 | Jesse Tannehill | .857 | 1894-1910 | |
| 3 | Joe Wood# | .750 | 1908-1916 | |
| 4 | Christy Mathewson | .700 | 1900-1916 | |
| 5 | Addie Joss | .667 | 1902-1910 | |
| 6 | Mordecai Brown | .571 | 1903-1916 | |
| 7 | Charles Bender# | .538 | 1903-1916 | |
| 8 | Red Ames# | .500 | 1903-1916 | |
| 8 | Dutch Leonard# | .500 | 1913-1916 | |
| 8 | Orval Overall | .500 | 1905-1913 | |
| 8 | Deacon Phillippe | .500 | 1899-1911 | |
| 8 | Eddie Plank# | .500 | 1901-1916 | |
| 13 | Cy Young* | .429 | 1890-1911 | |
| 14 | Rube Waddell | .400 | 1897-1910 | |
| 15 | Rube Marquard# | .333 | 1908-1916 | |
| 16 | Bill Bernhard | .250 | 1899-1907 | |
| 16 | Jack Pfiester | .250 | 1904-1911 | |
| 18 | Jeff Tesreau# | .200 | 1912-1916 | |
| 19 | Vean Gregg# | .167 | 1911-1916 | |
| 20 | Otto Hess | .000 | 1902-1914 |
