In the 1970s Cudmore was one of the first sailors to travel the world to compete at international yachting events, especially match racing. In 1986 he became the first non-American to win the Congressional Cup. In the America's Cup Cudmore was heavily involved in several British campaigns during the 1980s. He was also head coach of the 1992 winning campaign America3 and coach for the all-women's campaign in 1995.
Between 1977 and 1993 Cudmore took part in seven editions of the Admiral's Cup - Racing for Ireland, Great Britain, Australia and Germany. In 1989 he was the mastermind ashore for the victorious British team. To this day, Harold Cudmore travels the world, racing in a wide variety of inshore and offshore events. His amazing abilities as a yachtsman are only matched by his talent for storytelling!