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. In 2005 he was Match Race World Champion. In 2010, as skipper and helmsman for BMW Oracle Racing, Spithill became the youngest ever winner of the America's Cup. He led an amazing defense of the America's Cup 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.
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.
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. 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 main 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 5 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.
Spithill was the helmsman and skipper for the challenging team BMW Oracle Racing 90 in the 2010 America's Cup. His yacht USA beat the defending yacht Alinghi 5 by a considerable margin and Spithill became the youngest ever winner of the America's Cup. Most observers stated that USA 17's rigid wing sail had given it a decisive advantage.
Spithill currently holds the position of Skipper and Helmsman of Oracle Team USA's two AC72's 17 and Oracle Team USA 17.  On October 6, 2012, while at the helm of the Oracle USA AC45 yacht, Spithill managed to pitch-pole it. And again, at the helm of the Oracle USA AC72 yacht during a practice run on October, 16, 2012, Spithill pitch-poled it again. The subsequent capsizing caused $2 million worth of damage to the $10 million vessel.
During the 2013 season of the America's Cup, Oracle Team USA was the center of controversy as a member of Spithill's crew aboard the AC72 yacht, Dirk de Ridder, was found guilty of illegal modifications to the AC45 craft used earlier in the race. Oracle Team USA was subsequently ordered to pay a fine of $250,000 and to eject de Ridder from the crew (much to the dismay of Jimmy Spithill).
- http://www.americascup.com/en/actualite/news/first-blood-to-usa-19-2362[dead link]
- http://www.americascup.com/en/actualite/news/usa-win-33rd-america-s-cup-match-19-2827[dead link]
- "La démonstration de puissance d’Oracle brise le rêve d’Alinghi | Tribune de Genève". Tdg.ch. 2010-02-13. Retrieved 2013-09-07.
- "Team Member". Oracle-team-usa.americascup.com. Retrieved 2013-09-07.
- "ORACLE TEAM USA Spithill Capsize #acboathouse". YouTube. Retrieved 2013-09-07.
- "oracle 17 capsize". YouTube. 2012-09-06. Retrieved 2013-09-07.
- Andrew Dalton (2012-10-17). "Yacht-enfreude: Oracle Capsizes Their Fanciest Sailboat Yet". SFist. Retrieved 2013-09-07.
- "Oracle Team USA fined and penalised for AC World Series cheating". The Daily Sail. 2013-09-03. Retrieved 2013-09-03.
- "America's Cup champion Oracle docked 2 points". Yahoo!. 2013-09-03. Retrieved 2013-09-03.
|Wikimedia Commons has media related to James Spithill.|
- Italian page about America's Cup (Italian)
- Article about James Spithill
- YouTube video showing Oracle USA AC45 pitch-pole on October 6th during the 2012 America's Cup
- YouTube video showing Oracle USA AC72 pitch-pole on October 16th during a practice run for the 2012 America's Cup
- Article about damage to Oracle USA's AC72 yacht during a practice run on October 16, 2012
- Oracle Team USA fined and penalised for AC World Series cheating