In 2003 he led Oneworld in the America's Cup, reaching the semifinal of the Louis Vuitton Cup, where he was beaten by Oracle BMW Racing.
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Spithill was the helmsman and skipper for the challenging team BMW Oracle Racing 90 in the 2010 America's Cup.
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Spithill was next chosen by Francesco De Angelis, whom he had beaten in the 2003 Louis Vuitton quarter-finals, as his heir as helmsman of Luna Rossa Challenge in the 2007 America's Cup.
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He confirmed his ability by winning numerous races in the following years, including twice the Nations Cup (2003 and 2004), and obtaining a second place in the 2003 Match Race World Championship.
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