Knollwood was a pioneer among American golf clubs, one of the first fifteen to join the U.S.G.A. as allied members after the initial group of five founding clubs. In 1897, Knollwood became a charter member of the M.G.A., represented at the organizational meetings by Lawrence Van Etten and P.G. Thebaud.

A group of visiting professionals in 1896. Horace Rawlings, youthful winner of the first U.S. Open, is seated second from the left.

Despite its lack of length, the old Knollwood course lacked nothing in status. The club staged a semi-annual invitational tournament of major
import, one of the first of its kind, starting in November of 1895. One part of the competition was for the Knollwood Handicap Challenge Cup, the other was played at scratch for the Archbold Cup, and attracted the leading players of the day.

Prominent participants prior to the turn of the century were Arthur Fenn, Walter Travis, and Findlay Douglas Fenn, who played out of the Palmetto Golf Club in Aiken, Georgia, won twice in 1897, lowering the amateur course record to 77 in the spring meet, then to 76 in the fall before besting Douglas 5&4 in the finals. Within a couple of years, Fenn became the first American-born golf professional.

Travis was an early winner of the Handicap Cup, as was Arthur Livermore, a member of St. Andrew's original Apple Tree Gang. In 1898, Travis was medalist (at 163) in the 36-hole qualifying rounds, then shot 78 to win the final match. He went on to win three U.S.Amateurs (1900, 1901, and 1903), the 1904 British Amateur, and four Met Amateurs (1900, 1902, 1909, and 1915). He won again at Knollwood in 1903, this time lowering the course record, amateur or professional, to 71 in the qualifying rounds.

The 1904 tournament was won by C.G. Rowe, a publinx player from Van Cortlandt Park. Runnerup was steel magnate Andrew Carnegie of St. Andrew's, who lost on the 37th hole.

Knollwood fielded a strong team prior to the turn of the century, one that beat the powerful Fairfield County Golf Club (now Greenwich Country Club) team headed by Findlay Douglas in 1897 (Douglas won the U.S. Amateur in 1898). The Knollwood team was led by Herbert M. Harriman, who, in 1899, became the first American to win the U. S. Amateur, and also won the inaugural Met Amateur that same year, registering from Meadow Brook, where he also was a member. The Knollwood team also included J.B. Tailer, P.G. Thebaud, J.B.
Harriman, A.B. Kelley, F.A. Walthew, and N.C. Reynal, who was the captain.

Knollwood also staged an open tournament for women in 1898. A field of 39 started, although only 27 returned scorecards, the other dozen shooting embarrassingly high scores. U.S. Women's Amateur titleholder Beatrix Hoyt, 18 years old at the time, shot the day's low score (101), although losing the handicap contest.

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