Raynor designed over 100 golf courses during his career. His best known work includes, but is not limited to (* = with Charles B. Macdonald):

UNITED STATES:
Blue Mound, WI (1924, current layout) / Camargo, OH (1925) / Chicago GC, IL (1923, modifications) / Creek Club, NY (1923*) / CC of Fairfield, CT (1920) / Fishers Island, NY (1926, with Charles Banks) / Fox Chapel, PA (1923) / Greenbrier, WV (1924, Greenbrier course) / Lookout Mountain, GA (1923, completed by Charles Banks) / Monterey Peninsula, CA (1925*, Dunes course) / North Palm Beach, FL (1926) / Shinnecock Hills, NY (1901, redesign*) / Shoreacres, IL (1916); Waialae CC, HI (1927, with Charles Banks) / Yale University, CT (1923, with advice from C.B. Macdonald) / Yeamans Hall, SC (1925).

CARIBBEAN:
Mid Ocean Club, Bermuda (1921*).

During his relatively short career Raynor designed over 100 golf courses, but wrote very little about any of them or about golf architecture in general. He learned his craft from Charles Blair Macdonald, the first great golf course architect born in North America.

After studying civil engineering at Princeton University, Raynor worked in this field for almost 10 years. Aged 33, he was hired by Charles Blair Macdonald to survey the land on which the National Golf Links of America would be laid out. This project began a close working relationship, which lasted up until Raynor's early death in 1926.

Raynor's first solo design did not come until 1914, when he was already 38. In 1915 Macdonald handed his design business to Raynor, whose own career then began to flourish. His layouts were opening at a rapid pace, mostly up and down the eastern seaboard, but also as far away as Hawaii with Waialae CC. In the 12 years from 1914 Raynor designed over 100 courses, before contracting pneumonia on a visit to Florida. He was aged just 51 when he died.