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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Cy Young | 513 | 1890-1911 | |
| 2 | Kid Nichols* | 394 | 1890-1906 | |
| 3 | Christy Mathewson# | 324 | 1900-1914 | |
| 4 | Charles Bender# | 286 | 1903-1914 | |
| 4 | Eddie Plank# | 286 | 1901-1914 | |
| 6 | Jack Powell | 266 | 1897-1912 | |
| 7 | Gus Weyhing | 264 | 1887-1901 | |
| 8 | Amos Rusie | 246 | 1889-1901 | |
| 9 | Clark Griffith | 234 | 1891-1911 | |
| 10 | Bill Donovan# | 220 | 1898-1914 | |
| 11 | Addie Joss | 217 | 1902-1910 | |
| 12 | Rube Waddell | 215 | 1897-1910 | |
| 12 | Ed Walsh# | 215 | 1904-1914 | |
| 14 | Red Ames# | 212 | 1903-1914 | |
| 15 | Vic Willis | 209 | 1898-1910 | |
| 16 | Mordecai Brown# | 206 | 1903-1912 | |
| 16 | Doc White | 206 | 1901-1912 | |
| 18 | Al Orth | 200 | 1895-1909 | |
| 19 | Jesse Tannehill | 199 | 1894-1910 | |
| 20 | Deacon Phillippe | 190 | 1899-1911 | |
| 21 | Brickyard Kennedy | 188 | 1892-1903 | |
| 22 | Harry Howell | 185 | 1898-1909 | |
| 23 | Bob Ewing | 182 | 1902-1910 | |
| 24 | Pink Hawley | 181 | 1892-1901 | |
| 25 | Jack Chesbro | 180 | 1899-1909 | |
| 26 | Joe McGinnity | 176 | 1899-1908 | |
| 27 | Earl Moore | 175 | 1901-1913 | |
| 28 | Bill Dinneen | 173 | 1898-1909 | |
| 29 | Hooks Wiltse | 172 | 1904-1914 | |
| 30 | Red Donahue | 166 | 1893-1906 | |
| 31 | Walter Johnson# | 162 | 1907-1914 | |
| 32 | Ted Breitenstein | 160 | 1891-1901 | |
| 32 | Frank Kitson | 160 | 1898-1907 | |
| 34 | George Cuppy | 159 | 1892-1901 | |
| 35 | Joe Williams# | 155 | 1907-1914 | |
| 36 | Babe Adams# | 153 | 1906-1914 | |
| 37 | Bill Bernhard | 151 | 1899-1907 | |
| 38 | Noodles Hahn | 149 | 1899-1906 | |
| 39 | Jose Mendez# | 148 | 1907-1914 | |
| 40 | Chick Fraser | 147 | 1896-1909 | |
| 41 | Bert Cunningham | 143 | 1887-1901 | |
| 41 | Nap Rucker# | 143 | 1907-1914 | |
| 43 | Tom Hughes | 139 | 1900-1913 | |
| 44 | Kid Gleason | 138 | 1888-1911 | |
| 45 | Jack Pfiester | 135 | 1904-1911 | |
| 46 | Barney Pelty | 134 | 1903-1912 | |
| 47 | Eddie Cicotte# | 133 | 1906-1914 | |
| 48 | Tully Sparks | 132 | 1897-1909 | |
| 49 | Frank Smith | 130 | 1904-1911 | |
| 50 | Cy Falkenberg# | 129 | 1904-1914 | |
| 51 | Joe Wood# | 128 | 1908-1914 | |
| 52 | George McQuillan# | 127 | 1907-1914 | |
| 53 | Lefty Leifield# | 125 | 1905-1913 | |
| 54 | Roy Patterson | 123 | 1901-1907 | |
| 54 | Charlie Smith | 123 | 1903-1914 | |
| 56 | Rube Marquard# | 121 | 1908-1914 | |
| 57 | George Mullin | 120 | 1902-1913 | |
| 58 | Sam Leever | 118 | 1898-1909 | |
| 58 | Slim Sallee# | 118 | 1908-1914 | |
| 60 | Win Mercer | 117 | 1894-1902 | |
| 61 | Howie Camnitz | 115 | 1904-1913 | |
| 61 | Kid Carsey | 115 | 1891-1901 | |
| 63 | Frank Owen | 110 | 1901-1909 | |
| 64 | Jim Scott# | 109 | 1909-1914 | |
| 65 | Ed Siever | 106 | 1901-1908 | |
| 66 | Orval Overall | 101 | 1905-1913 | |
| 67 | Frank Foreman | 100 | 1884-1902 | |
| 68 | Ray Collins# | 99 | 1909-1914 | |
| 69 | Claude Hendrix# | 97 | 1911-1914 | |
| 70 | Art Fromme# | 96 | 1906-1914 | |
| 70 | Wiley Piatt | 96 | 1898-1903 | |
| 72 | Doc Newton | 95 | 1900-1909 | |
| 73 | Joe Lake | 94 | 1908-1913 | |
| 74 | Jack Coombs# | 93 | 1906-1914 | |
| 74 | Otto Hess# | 93 | 1902-1914 | |
| 74 | Bill Phillips | 93 | 1890-1903 | |
| 77 | Bill Hoffer | 91 | 1895-1901 | |
| 77 | Ted Lewis | 91 | 1896-1901 | |
| 77 | Cy Morgan | 91 | 1904-1912 | |
| 80 | Pastor Pareda# | 90 | 1910-1914 | |
| 81 | Nixey Callahan | 89 | 1894-1912 | |
| 81 | George Winter | 89 | 1901-1908 | |
| 83 | Ned Garvin | 88 | 1896-1904 | |
| 84 | Dummy Taylor | 87 | 1900-1908 | |
| 85 | Bob Groom# | 86 | 1909-1914 | |
| 86 | Larry Cheney# | 84 | 1911-1914 | |
| 86 | Al Maul | 84 | 1884-1900 | |
| 86 | Mike O'Neill | 84 | 1901-1906 | |
| 89 | Vean Gregg# | 83 | 1911-1914 | |
| 89 | Harry McIntire | 83 | 1905-1912 | |
| 89 | Jake Weimer | 83 | 1903-1909 | |
| 92 | Russ Ford | 82 | 1909-1913 | |
| 92 | Irv Young | 82 | 1905-1911 | |
| 94 | Andy Coakley | 81 | 1902-1910 | |
| 95 | Bugs Raymond | 80 | 1904-1910 | |
| 96 | Jay Hughes | 79 | 1898-1902 | |
| 96 | Ed Reulbach# | 79 | 1905-1914 | |
| 96 | Bob Wicker | 79 | 1901-1906 | |
| 99 | Ed Doheny | 78 | 1895-1903 | |
| 99 | Harry Krause | 78 | 1908-1911 |
