Scantlebury sailed with Digby Taylor on "NZI Enterprise" during the 1985–86 Whitbread Round the World Race. He raced with New Zealand Challenge on "KZ 7" in the 1987 Louis Vuitton Cup and sailed in the 1992 Louis Vuitton Cup. He joined Team New Zealand and was part of the crew that won the 1995 America's Cup on "NZL 32" and defended it in the 2000 America's Cup, where he was the boat building manager.