time the smallest winning margin in America's Cup history. Il Moro however, went on to lose this series 4–1. In 1995, Cayard joined an American effort for the America's Cup with Team Dennis Conner Stars & Stripes as primary helmsman. Though Stars & Stripes was noticeably slower than other boats on the defender series, the syndicate managed to win the 1995 Citizen Cup for the right to defend the Cup. In an unprecedented move, Team Dennis Conner decided to use the faster yacht Young America from the PACT 95 syndicate to defend the Cup. Cayard and this syndicate ended up losing the Cup 5–0 to Team New Zealand, who had won the 1995 Louis Vuitton Cup. With the change in venue and hemisphere for the Cup, the next America's Cup was not held until 2000. For the 2000 America's Cup, Cayard formed his own syndicate with backing from a number of sponsors and named it AmericaOne. The sponsoring yacht club was St. Francis Yacht Club of San Francisco. This syndicate competed against 14 challengers from 10 nations for the right to challenge for the Cup. AmericaOne reached the finals of the 2000 Louis Vuitton Cup racing against Prada for the right to challenge against Team New Zealand for the 2000 America's Cup. The final over the best of nine races was hotly contested, with neither yacht ever winning by more than two minutes. Prada won the first race, and AmericaOne the second. Prada went on to win the next two races, putting AmericaOne at a 3-1 disadvantage. AmericaOne then proceeded to win the next three races in a row and appeared on the brink of winning the Louis Vuitton Cup. However, equipment fatigue and failure proved decisive, several spinnakers were blown out, and Prada ended up winning the next two races and the series, 5–4, earning the right to challenge for the Cup. Prada ultimately lost in the America's Cup, 5–0 to the defender Team New Zealand. Following the conclusion of the 2000 America's Cup, Cayard recommended to the AmericaOne syndicate board of trustees that the syndicate should not compete for the 2003 America's Cup, citing significant financial and recruiting obstacles. Assets of AmericaOne were eventually sold to Larry Ellison who founded the Oracle Racing syndicate, later joining forces with BMW Racing to form Oracle BMW Racing, with Cayard as skipper. Cayard later was moved out of the skipper position