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 (2003 and 2004), 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 was at the time the youngest ever winner of the
America's Cup (30 years 7 months) until 2021 when
Peter Burling at 30 years 2 months became the youngest skipper to win 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 (awarded due to illegal boat modifications in the prior America's Cup World Series) 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, it was announced that Jimmy Spithill would join the Challenger of Record entry, Luna Rossa Challenge, for the
36th Americas Cup series. As one of two helmsmen, he steered the boat on starboard tack while
Francesco Bruni steered the boat on port tack. Luna Rossa won the
Prada Cup and lost in the
Americas Cup Finals to Team New Zealand in March 2021. Following defeat in the 2024 Louis Vuitton cup final against Ineos Brittana he announced his retirement from Americas Cup racing. == Incidents ==