Luna Rossa Prada Pirelli

Luna Rossa Prada Pirelli, originally named Prada Challenge, then Luna Rossa Challenge, is an Italian sailboat racing syndicate first created to compete for the 2000 America's Cup. It won the Louis Vuitton Cup in 2000 on its first attempt, but then lost the America's Cup match against the defending champion team, Team New Zealand.

Luna Rossa challenged again for the 2003 America's Cup but was knocked out in the semi-finals stage of the Louis Vuitton Cup. In the 2007 America's Cup, held in Valencia, Spain, the team reached the final of the Louis Vuitton Cup but was again defeated by Team New Zealand.

When the competition moved to AC72 catamarans for the 2013 America's Cup, held in San Francisco, Luna Rossa was the last team to challenge, entering a partnership with Team New Zealand. The Italian team reached the final of the Louis Vuitton Cup, losing to the Kiwi team. 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.

After Team New Zealand won the Cup back in 2017, Luna Rossa issued their challenge for the next edition, becoming the Challenger of Record for the 2021 America's Cup; after winning the Prada Cup, it lost 7-3 against the Kiwis.

The team is owned by Prada CEO Patrizio Bertelli and it is sponsored by that Italian fashion brand. Additional sponsors were Telecom Italia between 2005 and 2007 and Pirelli from 2018.

In February 1997, Prada CEO and avid sailor Patrizio Bertelli met with Argentinian yacht designer German Frers to discuss the construction of a cruising yacht. Frers asked suddenly "Why don’t we consider the America’s Cup?". Within 15 days, the core group behind Luna Rossa's first America's Cup campaign was established; the team challenged for the 30th America's Cup on behalf of the Yacht Club Punta Ala and under the name Prada Challenge.

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. After ranking first in the Round Robin stage by winning 26 out of 29 races, and first again in the knockout stage after winning 8 out of 10, Luna Rossa disputed the finals against AmericaOne, skippered by Paul Cayard. 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.

Having earned the right to challenge for the 2000 America's Cup, Luna Rossa lost 5–0 to defending Cup champion Team New Zealand.