While Luna Rossa planned to participate in the 2017 America's Cup, setting up a new base in Cagliari and starting development on the new boat, it withdrew from the competition in protest of the decision to switch the class of yachts to the AC50 catamaran.

Starting from October 1999 in Auckland, New Zealand, the team raced in the 2000 Louis Vuitton Cup with its two IACC yachts ITA-45 and ITA-48 (the latter only for the first two Round Robins) skippered by Francesco de Angelis.

In a long battle across 9 races, Luna Rossa ultimately prevailed 5–4, winning the Louis Vuitton Cup on 6 February 2000, the second time ever for an Italian team after Il Moro di Venezia in 1992.

Still skippered by Francesco de Angelis, Luna Rossa was eliminated in the semi-final stage by American team OneWorld.

The sailing team was enriched with new members, most notably Jimmy Spithill as helmsman, while Francesco de Angelis remained skipper.

During this series, Luna Rossa was skippered for the first time by Max Sirena, who had been mid-bowman in Luna Rossa's previous three America's Cup campaigns and had a key role as wing mast manager for BMW Oracle Racing's trimaran USA-17 that won the 2010 America's Cup.

In October 2011, Luna Rossa challenged for the 34th America's Cup on behalf of the Circolo della Vela Sicilia, based in Palermo.

The two boats, called Piranha and Swordfish, raced for the first time at the event in Naples between 11 and 15 April 2012 and were helmed by British sailors Chris Draper and Paul Campbell-James but with a primarily Italian crew, including skipper Max Sirena and Francesco Bruni as wing trimmer.

'Luna Rossa Piranha' went on to win the overall 2012/2013 season of the America's Cup World Series, following the disqualification of Oracle Team USA.

To overcome the late start in the 2013 America's Cup campaign, a deal was signed with Emirates Team New Zealand to share information on the design of their AC72 catamarans.

Luna Rossa Challenge, which was already in an advanced design stage for a yacht according to the original rule, withdrew in protest.

The Italian sailboat raced in the 2021 Prada Cup with a unique dual helmsmen configuration, with Jimmy Spithill on starboard and Francesco Bruni on port, while skipper Max Sirena stayed off the boat.

Since the 2007 America's Cup, all Luna Rossa boats have been built by Persico Marine in Nembro, Italy.