The Lesley Cup Matches began in 1905 at Garden City Golf Club in New York. Robert W. Lesley, a Philadelphian, proposed bringing together leading golfers from Boston, New York and Philadelphia for an annual inter-city competition, and a discussion of issues regarding the game of golf which was still in its infancy in America at that time. Lesley believed this yearly gathering would foster high standards for competition, sportsmanship, fellowship, and stewardship of the game. By the 1920s, the city teams had evolved into statewide teams from Massachusetts, Metropolitan New York and Pennsylvania. Quebec became the fourth jurisdiction later in the decade.

In the early years, the team rosters included many of the finest amateur players in the game. By the late 1940s, the professional golf tour had taken root, and the Lesley Cup teams came to be made up by very good players who were also leaders of local and state golf associations and prominent golf clubs. These qualifications still determine those selected to represent their jurisdictions.

The location of the annual match rotates among the four jurisdictions, with the current Captain of the host team responsible for all the details. Competition begins with 10 Singles Matches, one player from each team playing match play against a player from each of the other three teams in a foursome. A victory earns one point. A halved match earns ½ point. The Singles are followed by 5 Foursome Matches, with two-man teams playing alternate shot match play against each of three other two-man teams in an eightsome. Scoring is the same. The third and final round returns to 10 Singles Matches.

It is believed that the Lesley Cup format became the model for the Walker Cup and Ryder Cup Matches. The organization is governed by a Board consisting of three Trustees from each jurisdiction. The Board is chaired currently by Cary R. Jubinville of the Massachusetts Team, and he is known to all players as The Ghost (of Robert Lesley). The Ghost has principal responsibility for seeing that the traditions of keen competition, good sportsmanship and fellowship, and stewardship of the high standards of the game are upheld in such a way as to honor the memory of Robert W. Lesley, a giant in the early years of golf in America