Conner won the America's Cup four times, in 1974, 1980, 1987 and 1988, but was the first man ever to lose the famed Cup to a challenger, in 1983, as well as the first man to lose it twice. He was the skipper of the legendary Stars & Stripes boats. He also owns a shop, named Team Dennis Conner Team Shop.
Conner, sponsored by software company Computer Associates among others, was a rare non-billionaire fielding a team to compete in the 2003 America's Cup, held in New Zealand, despite receiving major checks of up to 40 million US dollars from his sponsors. He is known to like signing autographs for his fans. He is often referred to as Mr. America's Cup.