After some junior match race titles, in 1998 he arrived third in the Sydney-Hobart and first in the Kenwood Cup. He confirmed his ability by winning numerous races in the following years, including twice the Nations Cup, and obtaining a second place in the 2003 Match Race World Championship - and first place in 2005.
America's Cup
He debuted in the America's Cup in 2000 with Young Australia, showing his precocious talent despite leading an antiquated boat. At the age of 20, he was the youngest helmsman in the America's Cup. 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. For the 2007 America's Cup, Spithill was 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. Spithill was a mainstay of the team, which he led to the final of the Louis Vuitton Cup 2007 after beating one of the favourites, Oracle BMW Racing, 5–1 in the semifinals. He earned the nickname of "James Pitbull" among Italian fans because of his aggressive tactics during the pre-start phase of the races. He is the protagonist of what is arguably remembered as the greatest pre-start in the history of the America's Cup, forcing two penalties to BMW Oracle skipper Chris Dickson in race five of the Louis Vuitton Cup 2007, causing Dickson's resignation a few days later. Spithill went on to lose 5–0 to Emirates Team New Zealand in the 2007 Louis Vuitton Cup final. In 2010, as skipper and helmsman for BMW Oracle Racing, Spithill became the youngest ever winner of the America's Cup. Spithill was the helmsman and skipper for the challenging team BMW Oracle Racing 90 in the 2010 America's Cup. His yacht USA 17 beat the defending yacht Alinghi 5 by a considerable margin. Most observers stated that USA 17's rigid wing sail had given it a decisive advantage. He successfully defended in 2013, when Oracle Team USA came back from a −2 penalty score at the start to win 9–8 against Emirates Team New Zealand on the final race. In the 2017 America's Cup defence held in Bermuda, he also led Oracle Team USA, but lost eight races to one. In March 2018, Spithill announced he was returning to skipper the Challenger of Record entry, Luna Rossa Challenge, for the 36th Americas Cup series.
Incidents
On 6 October 2012, while at the helm of the Oracle USA AC45 yacht, Spithill managed to pitch-pole it. At the helm of the Oracle USA AC72 yacht during a practice run on 16 October 2012, Spithill pitch-poled it again. The subsequent capsizing caused US$2 million worth of damage to the $10 million vessel.
Personal life
Spithill is married to Jennifer Spithill. They have two sons.
