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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Ben OLeary# | 163 | 1886-1893 | |
| 2 | George Bauer# | 151 | 1886-1893 | |
| 3 | Lew Stiggers# | 141 | 1886-1890 | |
| 4 | David Roper# | 139 | 1888-1893 | |
| 5 | Oliver Rafferty# | 137 | 1884-1893 | |
| 6 | Ike Silsby# | 129 | 1888-1893 | |
| 7 | Hank Wolff# | 103 | 1886-1891 | |
| 8 | Clar Endicott# | 94 | 1886-1893 | |
| 8 | Jim Marchand# | 94 | 1886-1890 | |
| 10 | Al Marshall# | 90 | 1886-1891 | |
| 11 | Lew Townsel# | 82 | 1884-1887 | |
| 12 | Alonzo Fitzsimmons | 79 | 1885-1887 | |
| 13 | Walt Pelletier# | 74 | 1886-1893 | |
| 14 | Fred Cathey# | 73 | 1885-1887 | |
| 15 | Lou Scudder# | 66 | 1891-1893 | |
| 16 | Bob Livingston# | 61 | 1888-1893 | |
| 17 | Ernest Beale# | 59 | 1886-1891 | |
| 18 | Jeff Thomas# | 56 | 1891-1893 | |
| 19 | Denny McClister# | 53 | 1891-1892 | |
| 19 | Charley Reinhardt# | 53 | 1891-1893 | |
| 21 | John Dobbs# | 48 | 1892-1893 | |
| 22 | Stephen Fulton# | 47 | 1892-1893 | |
| 22 | Charley Pfeiffer# | 47 | 1892-1893 | |
| 24 | Charley Kearns# | 46 | 1892-1893 | |
| 24 | Vic Smith# | 46 | 1892-1893 | |
| 26 | Robert Stevens# | 42 | 1892-1893 | |
| 27 | Mike Flynn# | 41 | 1892-1893 | |
| 28 | Pat Tuckett# | 40 | 1886-1887 | |
| 29 | Buster Scott | 38 | 1884-1888 | |
| 30 | Jack Conley# | 37 | 1888-1890 | |
| 31 | Fred Wilder# | 36 | 1888-1892 | |
| 32 | Will Drouin# | 34 | 1892-1893 | |
| 32 | David Howard# | 34 | 1892-1893 | |
| 32 | Abel Rucker# | 34 | 1884-1885 | |
| 32 | Matt Thomas | 34 | 1886-1888 | |
| 36 | Phil Blackburn# | 33 | 1886-1891 | |
| 36 | Hank Gibson# | 33 | 1886-1891 | |
| 36 | Lucian Robinson | 33 | 1887-1888 | |
| 39 | Levi Atkins# | 32 | 1886-1893 | |
| 39 | Henry Bauer# | 32 | 1892-1893 | |
| 41 | John Sullivan# | 30 | 1892-1893 | |
| 42 | Edgar Kirkpatrick | 28 | 1891-1893 | |
| 42 | Henry Young | 28 | 1888-1889 | |
| 44 | Zeb Hase# | 27 | 1891-1893 | |
| 44 | Will Leduc# | 27 | 1886-1887 | |
| 46 | Herbert Monroe# | 26 | 1887-1893 | |
| 47 | Hal Redfield# | 25 | 1888-1893 | |
| 47 | Walt Trask# | 25 | 1886-1893 | |
| 49 | Cal Ames# | 24 | 1891-1893 | |
| 49 | Jacob Lewis | 24 | 1885-1885 | |
| 51 | Robert Antonelli# | 23 | 1893-1893 | |
| 51 | David Finney# | 23 | 1892-1893 | |
| 53 | Pierre Bouchard# | 22 | 1886-1891 | |
| 53 | Joe Whiteside# | 22 | 1884-1884 | |
| 55 | Will Truitt# | 21 | 1886-1887 | |
| 56 | Ben Eberhardt# | 20 | 1886-1891 | |
| 56 | Bob McDougall# | 20 | 1884-1887 | |
| 58 | James Oden# | 19 | 1892-1893 | |
| 58 | Rufus Westcott# | 19 | 1888-1893 | |
| 60 | Ernest Reeves# | 17 | 1888-1893 | |
| 61 | Joe Hewitt# | 16 | 1888-1891 | |
| 61 | Claude Wall# | 16 | 1888-1893 | |
| 63 | Silas Lawton# | 15 | 1884-1884 | |
| 63 | Pat Rowe# | 15 | 1886-1886 | |
| 63 | Tom Scott# | 15 | 1886-1891 | |
| 63 | Ben Sumlin# | 15 | 1888-1889 | |
| 67 | John Bates | 14 | 1888-1889 | |
| 68 | Ray Bramlett# | 11 | 1886-1889 | |
| 68 | Sam Grantham# | 11 | 1889-1893 | |
| 68 | Tim Grigg# | 11 | 1891-1893 | |
| 68 | Tom McCord | 11 | 1889-1890 | |
| 72 | Mike Dermer# | 10 | 1891-1893 | |
| 72 | Frank Gibson# | 10 | 1892-1893 | |
| 72 | Burt Godwin# | 10 | 1891-1893 | |
| 72 | Harry Hamilton | 10 | 1889-1890 | |
| 72 | Sherman Lenox | 10 | 1886-1887 | |
| 72 | Herbert Reich# | 10 | 1887-1887 | |
| 72 | Hiram Whitman | 10 | 1886-1888 | |
| 79 | Roy Becker# | 9 | 1884-1890 | |
| 79 | John Hammond | 9 | 1887-1887 | |
| 79 | Abel Haviland# | 9 | 1886-1893 | |
| 82 | Eddie Agee | 8 | 1884-1885 | |
| 82 | Sam Clarke# | 8 | 1888-1888 | |
| 82 | Hank Lilly# | 8 | 1888-1889 | |
| 82 | Glenn McKellar# | 8 | 1892-1893 | |
| 82 | Jim Ratliff# | 8 | 1892-1893 | |
| 87 | Daniel Johannes# | 7 | 1892-1893 | |
| 87 | Vic Kenyon# | 7 | 1886-1886 | |
| 87 | Dennis Kerrigan# | 7 | 1892-1893 | |
| 90 | Walt Gilman | 6 | 1888-1888 | |
| 90 | George Grey# | 6 | 1886-1887 | |
| 90 | Ned Leighton# | 6 | 1891-1891 | |
| 90 | Nate Pickett# | 6 | 1884-1884 | |
| 90 | Robert Roose# | 6 | 1892-1893 | |
| 90 | Elmer Trahan# | 6 | 1892-1893 | |
| 90 | Phil Walker | 6 | 1888-1888 | |
| 97 | Al Batiste# | 5 | 1886-1891 | |
| 97 | Ray Browne# | 5 | 1886-1886 | |
| 97 | Davey Clark | 5 | 1886-1886 | |
| 97 | Gene Flaherty# | 5 | 1886-1886 |
