1958 - Colombia (USA) def. Sceptre (UK) - 4 / 0

The British had hoped to have an edge by sailing 12-meter sailboats, which were raced actively in Britain, but not in the U.S. However, designer Olin Stephens was no stranger to the class, having designed what was arguably the fastest 12-meter in the world, Vim. His Columbia proved even faster in the summer trials, and in four races never trailed Hugh Goodson’s Sceptre.

1962 - Weatherly (USA) def. Gretel (Australie) - 4 / 1

Australian media magnate Sir Frank Packer was the first challenger from south of the equator. His sailboat Gretel, designed by Alan Payne, is generally regarded the faster sailboat, but managed only a single victory, the second race of the best-of-seven series. Weatherly, designed by Philip Rhodes, won on clever tactics by skipper Emil "Bus" Mosbacher and crew. But this was just the beginning of the flurry of fierce challenges from "Down Under" that ultimately unseated the Cup from its pedestal in the NYYC.

1964 - Constellation (USA) def. Sovereign (UK) - 4 / 0

The British were back in 1964, but the David Boyd-designed Sovereign was completely out-classed by Constellation, which was designed by Olin Stephens and skippered by Bob Bavier. The closest Sovereign came was in the first race, losing by five and half minutes.

1967 - Intrepid (USA) def. Dame Pattie (Aus.) - 4 / 0

Considered by many to be the greatest 12-meter ever built, the Olin Stephens-designed Intrepid took on Australia’s Dame Pattie. With the exception of a brief moment in the second race, however, the determined crew from the Royal Sydney Yacht Squadron could only watch Intrepid’s stern as Bus Mosbacher sailed her to his second successful Cup defense.

1970 - Intrepid (USA) def. Grettel II (Aus.) - 4 / 1

The beginning of the multiple challenges, and newspaper magnate Frank Packer had to dispose of Baron Marcel Bich of France before engaging the previous winner, Intrepid. Gretel, a new design from Alan Payne, was the most competitive challenger yet, but good crew work aboard Intrepid and winning a controversial protest in the second race ensured yet another American victory. Packer did not go quietly, however, and his accusations of cheating against the NYYC—the door to Intrepid’s head had been removed, fairings were installed near Intrepid’s rudder, and Gretel |’s disqualification in Race 2—errupted in a war of words that initiated correspondence between the Australian consulate and the U.S. State Department. Nonetheless, finishing first in two races on the water made the Aussies more determined than ever to continue .

1974 - Courageous (USA) def. Southern Cross (Aus.) - 4 / 0

The transition from wooden to aluminum hulls and the first time an organized challenger elimination series was conducted. France’s Baron Bich was back with France I, but the French boat was no match for Southern Cross, designed by Bob Miller (who later made history under the name Ben Lexcen). The match itself was anti-climactical after the hottly contested defender trials between two-time winner Intrepid and Olin Stephen’s new aluminum-hulled Courageous, which quickly dispatched Alan Bond’s Southern Cross in four straight races. The refitted Intrepid, sailed by a West Coast syndicate headed by San Diego’s Gerry Driscoll, came within one race of becoming a three-time defender. .

1977 - Courageous (USA) def. Australia (Aus.) - 4 / 0

Like Columbia and Intrepid before her, Courageous became the third defender to win back-to-back America’s Cup matches. This time it was the flamboyant Ted Turner at the helm, having bested two new boats in the defender trials. Alan Bond was back with his new Australia, which emerged atop a fleet of five challenging sailboats that also included Baron Bich’s France II, Sweden’s Sverige and Gretel II. The match, however, was a replay of 1974, with Courageous winning four straight.

1980 - Freedom (USA) def. Australia (Aus.) - 4 / 1

This match marked Dennis Conner’s first Cup victory as a skipper, his sailboat Freedom defeating Alan Bond’s reworked Australia four races to one. It also set the stage for the showdown three years later. Serving as tactician to Australian skipper Sir James Hardy was John Bertrand, who became Conner’s nemisis in three year’s time. The challenger trials included Frenchman Baron Bich’s fourth and final challenge with France |I, skippered by Bruno Troublé, the first skipper to fall overboard during an America’s Cup race. Also entering the fray were Lawrie Smith’s Lionheart from Great Britain, and Sverige from Sweden.

1983 - Liberty (USA) is def. by Australia II (Aus.) - 3 / 4

It was only fitting that when the NYYC finally lost the Cup, it was the most closely fought match in the event’s history, and it went down to the final race. Alan Bond’s years of effort finally paid off, and he took the Victorian-era trophy, claimed by the upstart American’s 132 years earlier, to a new home at Royal Perth Yacht Club in Perth, Western Australia. Dennis Conner and Liberty won the first two races, John Bertrand and Australia | the third. The Americans recovered in the fourth, but knew they were in trouble in light air. The two-race American lead faded to a 3-3 tie by the end of the sixth race. And by the end of the seventh race, the Cup was in Australian hands, the boys from Down Under finishing 41 seconds ahead of Liberty and terminating the longest winning streak in the history of sport. .

1987 - Kookaburra (Aus.) is def. by Stars & Stripes (USA) - 0 / 4

In terms of the number of contestants, this still stands as the biggest America’s Cup regatta yet. There were four defense syndicates, and the challenger series for the Louis Vuitton Cup featured 13 sailboats representing a record six nations. Dennis Conner mounting a campaign that lasted more than three years, his curiously shaped Stars & Stripes emerged the victor in a hotly contested challenger elimination series and went on to rout the Australian defender, Kookaburra II, 4-0. Conner was now not only the first man to lose the Cup, he was the first to win it back as well. The America’s Cup was returning to America, but to a new—and controversial—home at San Diego Yacht Club. .

1988 - Stars & Stripes (USA) def. New Zealand (NZ) - 2 / 0

The 27th defense is the most contentious chapter in an event chronicled in controversy, and considered by many to be the low point in the history of the America’s Cup.

New Zealander Michael Fay issued a renegade challenge, specifying a sailboat double the size of a 12-meter, and demanding the race be held within the 10 months specified in the Deed of Gift. When SDYC officials declared the challenge invalid, Fay took them to court and won the first round.

The SDYC responded by building a 60-foot wing-sailed catamaran as the defender against Fay’s 133-foot "Big Boat." It was a laugher on the water, as Conner’s Stars & Stripes easily defeated New Zealand, 2-0.

But things were deadly serious on shore, as the lawyers picked up where the sailors left off. Ranting ""Read the Deed," Fay returned to the New York Supreme Court, trustee of the America’s Cup Deed of Gift, where he asked that SDYC’s victory be overturned. Judge Carmen Ciparick granted his request. Not giving up without a fight, SDYC appealed the ruling to the New York Court of Appeals, and on April 26, 1990, SDYC was finally declared the winner of the match held more than a year and half earlier.