Dickson appeared on the America's Cup scene in 1987 when he was skipper of New Zealand’s first America's Cup challenge KZ 7 in the 1987 America's Cup at Fremantle, Australia. He was beaten that year by the eventual winner Dennis Conner and "Stars &amp; Stripes 87" in the Louis Vuitton Cup Final after winning 33 of 34 races in the round-robin phases and sweeping "French Kiss" 4–0 in the semi-finals.