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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | L | YEAR | Open Postseason Leaderboard |
|---|---|---|---|---|
| 1 | Bob Caruthers | 8 | 1884-1892 | |
| 2 | Dave Foutz | 6 | 1884-1896 | |
| 2 | Carl Hubbell# | 6 | 1928-1941 | |
| 2 | Silver King | 6 | 1886-1897 | |
| 5 | John Clarkson | 5 | 1882-1894 | |
| 5 | Lefty Grove# | 5 | 1925-1941 | |
| 5 | Waite Hoyt | 5 | 1918-1940 | |
| 5 | Sad Sam Jones | 5 | 1914-1936 | |
| 5 | Rube Marquard* | 5 | 1908-1924 | |
| 5 | Christy Mathewson* | 5 | 1900-1916 | |
| 5 | Eddie Plank* | 5 | 1901-1917 | |
| 12 | Chief Bender* | 4 | 1903-1917 | |
| 12 | Mordecai Brown* | 4 | 1903-1916 | |
| 12 | Bill Donovan | 4 | 1898-1918 | |
| 12 | Burleigh Grimes | 4 | 1916-1932 | |
| 12 | Ed Summers | 4 | 1908-1912 | |
| 12 | Adonis Terry | 4 | 1884-1897 | |
| 12 | Rube Walberg | 4 | 1923-1936 | |
| 19 | Ralph Buxton# | 3 | 1937-1940 | |
| 19 | Tex Carleton# | 3 | 1932-1941 | |
| 19 | Ice Box Chamberlin | 3 | 1886-1896 | |
| 19 | Eddie Cicotte* | 3 | 1905-1920 | |
| 19 | Dizzy Dean# | 3 | 1930-1941 | |
| 19 | Paul Derringer# | 3 | 1931-1941 | |
| 19 | George Earnshaw | 3 | 1928-1937 | |
| 19 | Red Faber* | 3 | 1914-1931 | |
| 19 | Tim Keefe | 3 | 1880-1893 | |
| 19 | Tom Lovett | 3 | 1885-1894 | |
| 19 | Ted Lyons# | 3 | 1923-1941 | |
| 19 | Carl Mays | 3 | 1915-1928 | |
| 19 | Jim McCormick | 3 | 1878-1887 | |
| 19 | George Mullin | 3 | 1902-1915 | |
| 19 | Roy Parmelee# | 3 | 1930-1940 | |
| 19 | Jack Pfiester | 3 | 1903-1911 | |
| 19 | Jack Quinn | 3 | 1909-1928 | |
| 19 | Jimmy Ring | 3 | 1917-1930 | |
| 19 | Mike Ryba# | 3 | 1935-1941 | |
| 19 | Slim Sallee | 3 | 1908-1924 | |
| 19 | Jeff Tesreau | 3 | 1912-1918 | |
| 19 | Ted Trent | 3 | 1937-1939 | |
| 19 | Bill Walker# | 3 | 1927-1938 | |
| 19 | Lefty Williams | 3 | 1913-1920 | |
| 19 | Cy Young* | 3 | 1890-1911 | |
| 44 | Jack Bentley | 2 | 1913-1926 | |
| 44 | Rube Benton | 2 | 1910-1930 | |
| 44 | Bullet Joe Bush | 2 | 1912-1928 | |
| 44 | Pete Conway | 2 | 1885-1889 | |
| 44 | Mort Cooper# | 2 | 1938-1941 | |
| 44 | Stan Coveleski | 2 | 1912-1927 | |
| 44 | Ed Crane | 2 | 1884-1893 | |
| 44 | Ed Daily | 2 | 1885-1891 | |
| 44 | Bill Doak | 2 | 1912-1929 | |
| 44 | Willie Foster | 2 | 1931-1939 | |
| 44 | Pretzels Getzien | 2 | 1884-1892 | |
| 44 | Bill Hallahan | 2 | 1926-1938 | |
| 44 | Slim Harriss | 2 | 1920-1936 | |
| 44 | Joe Heving# | 2 | 1930-1941 | |
| 44 | Thornton Lee# | 2 | 1933-1941 | |
| 44 | Sam Leever | 2 | 1898-1910 | |
| 44 | Johnny Marcum# | 2 | 1933-1940 | |
| 44 | Walt Masterson# | 2 | 1939-1941 | |
| 44 | Johnny Morrison | 2 | 1920-1931 | |
| 44 | Art Nehf | 2 | 1915-1930 | |
| 44 | Buck O'Brien | 2 | 1911-1913 | |
| 44 | Bob Osborn | 2 | 1925-1931 | |
| 44 | Deacon Phillippe | 2 | 1899-1911 | |
| 44 | Hal Schumacher# | 2 | 1931-1941 | |
| 44 | Bob Shawkey | 2 | 1913-1928 | |
| 44 | Sherry Smith | 2 | 1911-1927 | |
| 44 | Vito Tamulis# | 2 | 1934-1941 | |
| 44 | Tommy Thomas | 2 | 1926-1936 | |
| 44 | Hippo Vaughn* | 2 | 1908-1925 | |
| 44 | Mickey Welch | 2 | 1880-1892 | |
| 74 | Pete Alexander* | 1 | 1911-1929 | |
| 74 | Johnny Allen# | 1 | 1932-1941 | |
| 74 | Nick Altrock | 1 | 1898-1919 | |
| 74 | Red Ames | 1 | 1903-1919 | |
| 74 | Fred Anderson | 1 | 1909-1918 | |
| 74 | Jim Bagby | 1 | 1912-1927 | |
| 74 | Lady Baldwin | 1 | 1884-1890 | |
| 74 | Win Ballou# | 1 | 1928-1936 | |
| 74 | Buck Becannon | 1 | 1884-1885 | |
| 74 | Ray Benge | 1 | 1926-1939 | |
| 74 | Joe A Berry# | 1 | 1937-1939 | |
| 74 | Josh Billings | 1 | 1928-1931 | |
| 74 | Don Brennan | 1 | 1933-1939 | |
| 74 | Marv Breuer# | 1 | 1939-1941 | |
| 74 | Chet Brewer# | 1 | 1934-1940 | |
| 74 | Johnny Broaca# | 1 | 1934-1939 | |
| 74 | Ray Brown# | 1 | 1935-1935 | |
| 74 | Leon Cadore | 1 | 1915-1926 | |
| 74 | Ray Caldwell | 1 | 1910-1924 | |
| 74 | Howie Camnitz | 1 | 1904-1915 | |
| 74 | Ben Cantwell# | 1 | 1927-1940 | |
| 74 | George Chalmers | 1 | 1910-1916 | |
| 74 | Andy Coakley | 1 | 1902-1911 | |
| 74 | Rip Collins | 1 | 1920-1933 | |
| 74 | Wilbur Cooper | 1 | 1912-1926 | |
| 74 | Nig Cuppy | 1 | 1892-1901 | |
| 74 | Paul Dean# | 1 | 1934-1940 |
