<P> Representing the San Diego Yacht Club, Conner returned to win the 1987 America's Cup . His yacht Stars & Stripes 87 earned the right to challenge by winning the 1987 Louis Vuitton Cup against an unprecedented field of 13 challenger syndicates . In the America's Cup regatta he faced defender Iain Murray sailing Kookaburra III, who had defeated Alan Bond's Australia IV in the defender selection trials . Stars & Stripes 87 defeated Kookaburra III four races to nil . </P> <P> Technology was now playing an increasing role in yacht design . The 1983 winner, Australia II, had sported the revolutionary winged keel, and the New Zealand boat that Conner had beaten in the Louis Vuitton Cup final in Fremantle was the first 12 - metre class to have a hull of fiberglass, rather than aluminum or wood . </P> <P> The 12 - metre class rules stipulated that the hull had to be the same thickness throughout and could not be made lighter in the bow and stern . The other challengers demanded that core samples be taken from the plastic hull to show its thickness . At one press conference Dennis Conner asked, "Why would you build a plastic yacht...unless you wanted to cheat?" Despite attempts to defuse the situation, the "cheating comment" added to the controversy surrounding the Louis Vuitton challenge races . Chris Dickson, skipper of the Kiwi Magic (KZ 7), took the controversy in stride and with humor, and Conner has subsequently stated his regret over his comment . New Zealand syndicate head Sir Michael Fay's comment was that core samples would be taken "over my dead body". Eventually some small holes were drilled to test the hull, and ultrasonic testing was done to rule out air pockets in the construction . The boat was found to be within class rules, and the issue was set aside . Fay ceremoniously lay down in front of the measurer before the samples were taken . </P> <P> In 1987, soon after Conner had won back the cup with Stars and Stripes but before the San Diego Yacht Club had publicly issued terms for the next regatta, a New Zealand syndicate, again led by merchant banker Sir Michael Fay, lodged a surprise challenge . Fay challenged with a gigantic yacht named New Zealand (KZ1) or the Big Boat, which with a 90 - foot (27 m) waterline, was the largest single masted yacht possible under the original rules of the cup trust deed . This was an unwelcome challenge to the San Diego Yacht Club, who wanted to continue to run Cup regattas using 12 - metre yachts . A legal battle ensued over the challenge, with Justice Carmen Ciparick of the New York State Supreme (trial) Court (which administers the Deed of Gift) ruling that Fay's challenge on behalf of Mercury Bay Boating Club (MBBC) was valid . The court ordered SDYC to accept it and negotiate mutually agreeable terms for a match, or to race under the default provisions of the Deed, or to forfeit the cup to MBBC . </P>

Who won the very first cup match in 1902