The Association's Junior team compete in the Williamson Cup Matches each August, with four players representing the WPGA in a thirty-six hole stroke play competition against eleven teams from the northeast and Canada. The team is selected on playing excellence throughout the championship season. The WPGA Williamson Cup team has never been victorious but has finished runner-up twice in the last decade. The WPGA has been competing in this annual event since 1968.

The Williamson Cup was established in 1964 by A. Fred Williamson, in memory of his father, one of the original founders of famed Winged Foot Golf Club and a long-time member of the USGA Executive Committee.

The inaugural event was fittingly held at Winged Foot, and was contested by the four charter Williamson Cup Association Members from Metropolitan New York, Philadelphia, Washington D.C. and Buffalo. Three of the four original cities won the opening three Cup Matches: Washington (at Winged Foot G.C.) in 19674, Metropolitan New York (at Chevy Chase Club) in 1995, and Buffalo (at Atlantic City C.C.) in 1966.

By 1968, the Williamson Cup had already attained international regard as well as wider recognition in the United States. In that year, teams were entered by the Provinces of Quebec and Ontario, Canada, and by Western Pennsylvania. In face, in its first Williamson Cup Match, the Ontario team won on the first hole of a sudden death playoff at Garden City C.C. to become the first international victor. The Ligue d'Paris (France) participated in 1995, which further extended the unique flavor of the event.

Over the years, lasting friendships have developed between contestants and teammates. Fred Williamson envisioned that the Williamson Cup Matches would give a segment of the promising junior golfers of the day the experience of competition at national and international levels. Thanks to his foresight and to the support of the participating golf associations, and the contributions of the great cities involved, hundreds of young golfers have been better prepared for satisfying and enjoyable careers in amateur and professional golf.