The Rolex New York Yacht Club Invitational Cup is a biennial event hosted by the New York Yacht Club in Newport, R.I., in September at its Harbour Court Clubhouse. The Invitational Cup is a regatta for teams of amateur sailors representing yacht clubs from around the world. The competition was first run in 2009. Through the 2017 edition, the regatta was sailed in a fleet of one-design Swan 42 yachts. The New York Yacht Club Swan 42 was the eighth one-design class sponsored by the New York Yacht Club. Standardized rig tuning and identical sails make this regatta the most level platform for amateur competition in boats this size. 

The 2019 edition featured the debut of the IC37, a boat designed for this competition by Mark Mills Design and created by the New York Yacht Club. To ensure the most level playing field in international sailing, the Club purchased the first 20 IC37s and will use that fleet of perfectly matched yachts for the Invitational Cup for the foreseeable future.

The host team, led by Phil Lotz (NYYC Commodore, 2017 and 2018) won the inaugural competition, defeating 16 other clubs. The Royal Canadian Yacht Club (Toronto, Canada), led by Olympic silver medalist Terry McLaughlin, won in 2011 and 2013, followed by the Royal Thames Yacht Club (London, England) in 2015 and Southern Yacht Club from New Orleans, La., in 2017. In 2019, world champion sailor Guido Belgiorno-Nettis and his crew from Australia's Royal Sydney Yacht Squadron became the first team from the Southern Hemisphere to win the Rolex New York Yacht Club Invitational Cup.

International yacht clubs apply to compete in the regatta. For United States yacht clubs, the path to the event is through the Resolute Cup, which is run on even years for domestic clubs and generally sailed in smaller one-design yachts. Teams from more than 40 yacht clubs from 21 countries and all six inhabited continents, more than 1,000 sailors, have competed in at least one edition of the Rolex New York Yacht Club Annual Regatta.