29 x 36-inch poster, 'America's Cup '88 San Diego', signed by the skipper Dennis Connor and the artist, James Costa: 'To Mayor Maureen O'Connor, XXVII Defense - San Diego '88'. The 1988 America's Cup was the 27th America's Cup, held in San Diego 7-9 September 1988, contested between the defender, San Diego Yacht Club's Stars and Stripes H3, and challenger, Mercury Bay Boating Club's New Zealand Challenge's KZ-1. The regatta was won by the San Diego Yacht club, two races to none.