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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 | 1884-1899 | |
| 2 | Harvey Holmes# | 241 | 1884-1897 | |
| 3 | Will Morrill# | 232 | 1886-1899 | |
| 4 | Vic Kenyon# | 224 | 1886-1897 | |
| 5 | Nate Mahoney | 201 | 1884-1898 | |
| 6 | Steve Thorpe# | 199 | 1886-1895 | |
| 7 | Herbert Goodwin# | 193 | 1886-1899 | |
| 7 | Fred Watton# | 193 | 1891-1899 | |
| 9 | Nate Pickett | 191 | 1886-1897 | |
| 10 | Jim Weber | 187 | 1886-1899 | |
| 11 | Ernie Kraus# | 186 | 1884-1899 | |
| 12 | Gus McGuire | 167 | 1884-1894 | |
| 13 | Ed Murdock# | 163 | 1888-1898 | |
| 14 | Pat Tuckett# | 161 | 1888-1894 | |
| 15 | Vic Montague# | 146 | 1886-1896 | |
| 16 | Pat Murphy | 145 | 1884-1892 | |
| 17 | Ned Flannery# | 143 | 1894-1899 | |
| 17 | Al Lynn# | 143 | 1888-1899 | |
| 19 | Lou Gibbs# | 128 | 1888-1899 | |
| 20 | Joe Kessler | 125 | 1886-1891 | |
| 20 | Win Redmond# | 125 | 1894-1899 | |
| 22 | Sam Tilden# | 123 | 1894-1899 | |
| 23 | Mike Sullivan# | 113 | 1895-1899 | |
| 24 | Jim Gallivan# | 111 | 1894-1899 | |
| 24 | George Grey# | 111 | 1888-1899 | |
| 26 | Ed Farley# | 105 | 1894-1899 | |
| 27 | George Mulligan# | 102 | 1884-1887 | |
| 28 | Will Truitt | 95 | 1888-1893 | |
| 29 | Bill Wainwright# | 92 | 1894-1899 | |
| 30 | Lew Townsel# | 90 | 1888-1890 | |
| 31 | Charley Pfeiffer# | 89 | 1888-1890 | |
| 32 | Herbert Crosby# | 82 | 1886-1892 | |
| 33 | Jim Sutherland# | 79 | 1894-1899 | |
| 34 | Ed Sharp# | 76 | 1896-1899 | |
| 35 | Willis McAdory | 74 | 1886-1888 | |
| 36 | Ben Trease | 73 | 1886-1890 | |
| 37 | Vic Caldwell# | 71 | 1895-1899 | |
| 37 | Fletcher Dabney# | 71 | 1897-1899 | |
| 39 | Frank Hawthorne# | 66 | 1894-1899 | |
| 40 | Frank Mulrooney# | 64 | 1896-1899 | |
| 40 | Harrison Wentworth# | 64 | 1894-1899 | |
| 42 | Ray Anson# | 63 | 1897-1899 | |
| 42 | Rufus Thomas# | 63 | 1884-1899 | |
| 44 | Robert Wojtowicz# | 61 | 1892-1895 | |
| 45 | Lou Blackwell# | 60 | 1894-1899 | |
| 45 | Frank Wilder# | 60 | 1896-1899 | |
| 47 | Bartholomew Becker# | 59 | 1892-1897 | |
| 47 | Sam Toole# | 59 | 1892-1899 | |
| 49 | Hiram Keys | 53 | 1884-1892 | |
| 50 | Sam Barksdale# | 52 | 1897-1899 | |
| 50 | Joseph Stone# | 52 | 1892-1897 | |
| 52 | Fred Cathey# | 51 | 1888-1889 | |
| 52 | Dan Farham | 51 | 1884-1885 | |
| 54 | Horatio Fry# | 50 | 1892-1896 | |
| 55 | Joe Delahanty# | 49 | 1895-1899 | |
| 55 | Joseph Wadsworth# | 49 | 1892-1894 | |
| 57 | Hank Lilly | 48 | 1884-1886 | |
| 57 | Joe Whiteside# | 48 | 1886-1887 | |
| 59 | Al Holloway# | 43 | 1896-1899 | |
| 60 | Marty Cosker# | 42 | 1891-1898 | |
| 61 | Thomas Churchville# | 40 | 1892-1899 | |
| 62 | Ray Browne | 37 | 1887-1889 | |
| 62 | Frank Hunter# | 37 | 1897-1899 | |
| 64 | Fred Pinckney | 33 | 1886-1887 | |
| 65 | Alfred Bush | 31 | 1884-1885 | |
| 66 | Henry Moody | 30 | 1884-1886 | |
| 67 | George Dillingham | 29 | 1884-1893 | |
| 67 | Al McDonough# | 29 | 1891-1897 | |
| 69 | Ed Fischer | 28 | 1891-1894 | |
| 69 | Rube Seidel# | 28 | 1896-1899 | |
| 71 | Hank Sherrod# | 27 | 1884-1898 | |
| 72 | Gene Carter | 25 | 1884-1885 | |
| 73 | James Carey# | 23 | 1897-1899 | |
| 73 | Gene Flaherty# | 23 | 1887-1892 | |
| 73 | Phil Hull# | 23 | 1886-1899 | |
| 73 | Lou Jewett# | 23 | 1891-1891 | |
| 73 | Mal King# | 23 | 1899-1899 | |
| 78 | Pop Carter# | 22 | 1899-1899 | |
| 78 | Bill Hanrahan# | 22 | 1895-1899 | |
| 78 | Guy Rauhauser# | 22 | 1899-1899 | |
| 81 | Roger Patterson# | 21 | 1897-1899 | |
| 81 | Frank Ward# | 21 | 1899-1899 | |
| 83 | Hank Gibson | 20 | 1886-1888 | |
| 83 | Lee Hein# | 20 | 1899-1899 | |
| 83 | Hank Weber# | 20 | 1896-1898 | |
| 83 | Henry Young | 20 | 1884-1884 | |
| 87 | Martin Hennington# | 19 | 1889-1899 | |
| 88 | Andy Chandler# | 18 | 1896-1899 | |
| 88 | Darren Kelly | 18 | 1886-1887 | |
| 88 | Denny McClister# | 18 | 1895-1899 | |
| 91 | Sam Clarke# | 17 | 1888-1894 | |
| 92 | Michael Drake# | 16 | 1899-1899 | |
| 92 | Joe Harding# | 16 | 1896-1899 | |
| 92 | Tom Scott | 16 | 1886-1887 | |
| 95 | Fred Burke# | 15 | 1888-1898 | |
| 95 | Henry King | 15 | 1884-1884 | |
| 95 | Michael Raines# | 15 | 1892-1893 | |
| 95 | Tom Tanner# | 15 | 1892-1899 | |
| 99 | Chester Loomis | 14 | 1888-1889 | |
| 100 | Buster Bauer# | 12 | 1896-1899 |
