[1] It was previously held in Long Island and New Haven before it was sold and relocated to Winston-Salem, creating a new tournament.

The event started on Long Island's Jericho hamlet as a four-player singles exhibition in 1981, the event, first known as the Hamlet Challenge Cup, developed into a larger draw competition, and saw winning numerous top players in the 1980s, including Ivan Lendl and an eighteen-year-old Andre Agassi in 1988.

[3][4][5][6][7][8][9][10][11] In 1990, the Long Island tournament became part of the tour as it entered the newly created Association of Tennis Professionals (ATP) Tour, being sponsored by numerous companies including; Norstar Bank in 1990 and 1991,[12] Waldbaum's from 1992 to 1995 and from 1997 to 2000,[12] Genovese Drug Stores in 1996,[13] and TD Waterhouse from 2002 until the move to New Haven,[14] adding names like Stefan Edberg, Yevgeny Kafelnikov, Magnus Norman, Paradorn Srichaphan and Lleyton Hewitt to its list of champions.

In 2005 the USTA decided to purchase the men's tournament of Long Island, New York and merge it with the Women's event at New Haven.

The only doubles team to win back-to-back titles is Jonathan Stark and Kevin Ullyett.