America's Cup Contestant is a term used to refer to a YACHTER who competes in the America's Cup, an international sailing competition. The America's Cup is the oldest active trophy in international sport and has been held since 1851. It is a match race between two sailing yachts, one representing the defending champion and the other representing the challenger. The winner of the race is the first to win two out of three races. Yachters who compete in the America's Cup are highly skilled sailors who have trained extensively for the event.