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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Otis Sheehan | 320 | 1884-1902 | |
| 2 | Ned Flannery# | 288 | 1894-1907 | |
| 3 | Harvey Holmes | 241 | 1884-1897 | |
| 4 | Will Morrill | 232 | 1886-1899 | |
| 5 | Ed Murdock# | 230 | 1888-1907 | |
| 6 | Vic Kenyon | 224 | 1886-1897 | |
| 7 | Ed Farley# | 218 | 1894-1907 | |
| 8 | Fred Watton | 212 | 1891-1902 | |
| 9 | Bill Wainwright# | 202 | 1894-1907 | |
| 10 | Nate Mahoney | 201 | 1884-1898 | |
| 11 | Steve Thorpe | 199 | 1886-1895 | |
| 12 | Herbert Goodwin | 194 | 1886-1900 | |
| 13 | Nate Pickett | 191 | 1886-1897 | |
| 14 | Jim Weber | 187 | 1886-1899 | |
| 15 | Fletcher Dabney# | 186 | 1897-1907 | |
| 15 | Jim Gallivan# | 186 | 1894-1907 | |
| 15 | Ernie Kraus | 186 | 1884-1903 | |
| 18 | Frank Mulrooney# | 178 | 1896-1907 | |
| 19 | Mike Sullivan# | 172 | 1895-1907 | |
| 20 | Gus McGuire | 167 | 1884-1894 | |
| 21 | Pat Tuckett | 161 | 1888-1894 | |
| 22 | Guy Rauhauser# | 160 | 1899-1907 | |
| 23 | Al Lynn | 159 | 1888-1904 | |
| 24 | Vic Montague | 146 | 1886-1896 | |
| 25 | Pat Murphy | 145 | 1884-1892 | |
| 26 | Win Redmond# | 137 | 1894-1907 | |
| 27 | Bert Connor# | 135 | 1900-1907 | |
| 28 | Lou Gibbs | 128 | 1888-1900 | |
| 29 | Sam Tilden# | 127 | 1894-1900 | |
| 30 | Frank Hawthorne# | 125 | 1894-1904 | |
| 30 | Joe Kessler | 125 | 1886-1891 | |
| 32 | Mark LaRue# | 115 | 1900-1907 | |
| 33 | Sam Barksdale | 111 | 1897-1907 | |
| 33 | George Grey | 111 | 1888-1900 | |
| 35 | Patsy Fitzgerald# | 105 | 1899-1907 | |
| 36 | Billy Stevens# | 104 | 1901-1907 | |
| 36 | Gene Sykes# | 104 | 1901-1907 | |
| 38 | Ray Anson# | 103 | 1897-1907 | |
| 39 | George Mulligan | 102 | 1884-1887 | |
| 40 | Vic Caldwell# | 101 | 1895-1907 | |
| 40 | Dad Zepley# | 101 | 1900-1907 | |
| 42 | Ed Sharp# | 96 | 1896-1907 | |
| 43 | Will Truitt | 95 | 1888-1893 | |
| 44 | Jim Sutherland | 92 | 1894-1907 | |
| 45 | Dan Reichert# | 91 | 1902-1907 | |
| 46 | Lew Townsel | 90 | 1888-1890 | |
| 47 | Charley Pfeiffer | 89 | 1888-1890 | |
| 48 | George Oldfield# | 85 | 1903-1907 | |
| 48 | Fred Vinson# | 85 | 1903-1907 | |
| 48 | Ellsworth Whatley# | 85 | 1902-1907 | |
| 51 | Jack Martino# | 84 | 1899-1907 | |
| 52 | Mal King# | 83 | 1899-1907 | |
| 52 | Clark Lamb# | 83 | 1902-1907 | |
| 54 | Herbert Crosby | 82 | 1886-1892 | |
| 55 | Bob Harris# | 80 | 1902-1907 | |
| 56 | Rube Harmonie# | 79 | 1903-1907 | |
| 57 | Frank Hunter# | 75 | 1897-1907 | |
| 58 | Willis McAdory | 74 | 1886-1888 | |
| 59 | Ben Trease | 73 | 1886-1890 | |
| 60 | Lou Blackwell# | 72 | 1894-1907 | |
| 61 | Sam Toole | 68 | 1892-1901 | |
| 62 | Harrison Wentworth# | 66 | 1894-1901 | |
| 63 | Charles Lindsey# | 63 | 1903-1907 | |
| 63 | Rufus Thomas | 63 | 1884-1904 | |
| 65 | Frank Wilder | 62 | 1896-1906 | |
| 66 | Norman Wade# | 61 | 1902-1907 | |
| 66 | Robert Wojtowicz | 61 | 1892-1895 | |
| 68 | Bartholomew Becker | 59 | 1892-1901 | |
| 69 | Miles Benton# | 58 | 1903-1907 | |
| 70 | Michael Drake | 56 | 1899-1907 | |
| 70 | Joe Harding# | 56 | 1896-1907 | |
| 72 | Orville Colby# | 53 | 1903-1907 | |
| 72 | Hiram Keys | 53 | 1884-1892 | |
| 74 | Pop Carter | 52 | 1899-1907 | |
| 74 | Joseph Stone | 52 | 1892-1897 | |
| 76 | Fred Cathey | 51 | 1888-1889 | |
| 76 | Dan Farham | 51 | 1884-1885 | |
| 78 | James Carey# | 50 | 1897-1907 | |
| 78 | Horatio Fry | 50 | 1892-1896 | |
| 80 | Joe Delahanty# | 49 | 1895-1905 | |
| 80 | Joseph Wadsworth | 49 | 1892-1894 | |
| 82 | Hank Lilly | 48 | 1884-1886 | |
| 82 | Joe Whiteside | 48 | 1886-1887 | |
| 84 | Al Holloway# | 43 | 1896-1902 | |
| 84 | Frank Ward# | 43 | 1899-1907 | |
| 86 | Andy Chandler# | 42 | 1896-1907 | |
| 86 | Marty Cosker | 42 | 1891-1898 | |
| 88 | Thomas Churchville | 41 | 1892-1901 | |
| 88 | Fred Wilson# | 41 | 1903-1904 | |
| 90 | Elias Woodbury# | 38 | 1900-1907 | |
| 91 | Ray Browne | 37 | 1887-1889 | |
| 91 | Roscoe Rush# | 37 | 1901-1907 | |
| 93 | Doc Coughlin# | 36 | 1903-1906 | |
| 93 | Bill Hanrahan# | 36 | 1895-1900 | |
| 93 | Ham Stringfellow# | 36 | 1901-1907 | |
| 96 | Theo Heath | 35 | 1900-1902 | |
| 97 | Heinie Durst# | 34 | 1903-1907 | |
| 97 | Heck Martinez# | 34 | 1903-1907 | |
| 99 | Fred Pinckney | 33 | 1886-1887 | |
| 100 | Bill Murtagh# | 32 | 1895-1907 |
