Conner has won the America's Cup three times, successfully defending the Cup in 1980, and 1988 and winning as the challenger in 1987. His 4-3 loss in 1983 to Australian Alan Bond's controversial wing-keeled challenger "Australia II" was the first Cup defender to be defeated in the 132-year history of the race, simultaneously ending a run by the New York Yacht Club that began with the first contest. Following the loss Conner formed his own syndicate, the Sail America Foundation, through which he raised funds to mount a challenge on behalf of the San Diego Yacht Club, culminating with winning the Cup back from Australia in 1987. Conner's 1983 loss and the subsequent 1987 victory are the basis of the 1992 American Zoetrope film "Wind".