His first significant win came in 1899 at the Southern California Open before he started his run at the
U.S. Open. In the 14 straight Opens that he played, Anderson won four, was second once, third once, fourth twice, fifth three times, 11th twice and 15th once. He won titles with both the old gutta-percha golf ball, and the rubber-cored ball which came into use in 1902. Anderson also won the
Western Open in 1902, 1904, 1908, and 1909; this tournament, the second-oldest in the U.S., was classified as a
PGA Tour event for most of its more than 100 years of operation, and is classified by some golf historians as a major championship during Anderson's era. Anderson's accuracy with all clubs, combined with his concentration under pressure, made him a formidable and highly respected competitor. Anderson made his living as a golf professional, working at ten different clubs in fourteen years. He listed the
Apawamis Club in
Rye, New York as his home course from 1901 through 1906. He played many exhibition challenge matches for stakes, in addition to tournaments. ==Death and legacy==