The 21 greatest America’s Cup moments, ranked — from Black Magic’s stunning upset of Team Dennis Conner in 1995, to Oracle Team USA’s dramatic comeback in 2013, to Team New Zealand’s 2017 pitchpole and everything in between.

Words: Michael Burgess
Design: Laura Hutchins

1992 — Bowsprit controversy 

This was the third challenge backed by Fay and New Zealand were ranked second from eight teams after the round robin series. 

Coutts and Butterworth replaced Rod Davis and David Barnes in the afterguard for the Louis Vuitton Cup, and New Zealand led Il Moro di Venezia 4-1 in the best-of-nine series. 

But after a protest about the use of the bowsprit on NZL20 was upheld, New Zealand lost one point and were compelled to remove the pole. 

The drama seemed to negatively affect the team, as well as the boat’s speed. They lost four consecutive races, albeit by close margins, and Paul Cayard’s Italian team went on to challenge Bill Koch’s America3 for the Cup. 

2000 & 2003 — Louis Vuitton Cups in New Zealand 

These were golden days for the Auckland sailing fraternity, with two compelling series, numerous challengers and plenty of storylines. 

The city was transformed for both regattas, with a buzz in the air and on the water. 

The 2000 America’s Cup attracted 11 challengers from seven nations, including the Aloha Racing team backed by the Waikiki Yacht Club (one of three teams from the United States), a first Swiss challenge and Young Australia, skippered by a 19-year-old James Spithill. 

Prada Challenge edged America One 5-4 in the Louis Vuitton Cup decider, with Team Dennis Conner narrowly missing the finals. 

Three years later Auckland’s waterfront hosted another wonderful sailing festival, with nine challengers from six countries. 

Conner’s assertion was a 1980s flashpoint, the moment he became “Dirty Den” in the eyes of many Kiwis. 

In his brash way, Conner was questioning the legality of the Farr-designed KZ7, with its world-first fibreglass hull, while all other teams favoured the traditional aluminium. 

KZ7 was cleared twice by the Cup’s official jury, but Conner’s remarks stung. 

But the American was also a wonderful sailor, exhibited once again in the Louis Vuitton Cup final. 

The New Zealand upstarts, in their first challenge, were favourites, having beaten Stars and Stripes twice during the round robin, when they finished as top qualifier. 

But Conner’s team had 13 years of experience, and were helped by heavier air during the finals. 

The Americans took the first two, before a battle for the ages in the third, with a record 55 tacks by Conner on one beat to windward, got New Zealand on the ledger. That was the high point though, as Stars and Stripes prevailed 4-1. 

2017 — Cyclists on the boat 

One of the most radical innovations in Cup history came in 2017, as Team New Zealand dispensed with the traditional grinders, who toiled away on hand-operated winches to adjust the sails, and instead used cyclists riding stationary bikes. 

The idea was dreamed up in 2014 and perfected over the next two years on the AC50 catamarans, as they employed 2012 Olympic bronze medallist Simon van Velthooven to provide cycling expertise, with former rower and Olympic champion Joseph Sullivan adding grunt to the pedal power. 

Their rivals were sceptical about the potential benefits, but the “cyclors” played a key role in the eventual triumph, adding extra, more consistent horsepower when it was needed most.

One of the greatest duels in Cup history came in race seven of the 2007 America's Cup finals. Team New Zealand had bested Luna Rossa Challenge after a gruelling Louis Vuitton campaign, which had featured 11 challengers. 

The Kiwis were underdogs against the experienced and heavily resourced Alinghi team but soon showed their mettle, winning the second and third races to go ahead 2-1. 

Alinghi won the next three, by margins of 30, 19 and 28 seconds. 

The next, and ultimately final race was a classic. After multiple lead changes throughout, Alinghi looked assured of victory when they rounded the final mark 12 seconds ahead. 

But on the final approach their spinnaker pole flew off the mast, stalling the Swiss boat. 

Team New Zealand took advantage, pushed by a dramatic wind shift, and surged ahead with 150 metres to go. But they had to complete a penalty turn before the finish line — and arguably left it too late — allowing Alinghi to sneak past and win by one second. 

“How many races of the century can we have in this regatta?” asked a stunned Montgomery on TVNZ, revelling in the greatest spectacle of the pre-foiling era. 

1987 — The summer of Kiwi Magic 

No boat has captured the nation’s imagination like KZ7, even allowing for the subsequent celebrated wins in 1995 and 2017. 

It was New Zealand’s first tilt at the America’s Cup, the start of an obsession, and the country had a rocket ship. 

The sense of patriotism ahead of the Fay-backed challenge had been fuelled by the hit single Sailing Away. 

A star-studded ensemble, including Dave Dobbyn, Billy T James, Tim Finn, Annie Crummer, Ray Woolf and Barry Crump, backed by a choir of sporting greats and celebrities, produced a song that spent nine weeks at No 1, the record for a local single until 2009. 

Fay had provided the funds, Farr the revolutionary design and Dickson the brash talent at the helm. 

And how she flew. KZ7 won a staggering 33 of 34 races in the round robin phase (the next best was 27 victories) to qualify as top challenger. 

The Kiwi crew, which included Butterworth, Tony Rae and Simon Daubney, then swept French Kiss 4-0 to reach the Louis Vuitton final. 

That was where the journey ended, but they still arrived home to a heroes’ welcome. 

The New York Yacht Club had held the America’s Cup for 132 years, the longest winning streak in sports history. 

Across the century only two challengers had gone close — Sir Thomas Lipton in 1920 (3-2) and Sir Thomas Sopwith in 1934 (4-2). 

Australia had mounted six campaigns since 1962, spearheaded by Sir Frank Packer (twice) and Alan Bond (three times) and had won the Louis Vuitton Cup five times to earn the right to challenge, but all had ended in defeat and disappointment on the waters of Newport, off Rhode Island. 

So 1983 was a sweet victory, a moment many Australians thought they would never see. 

Australia II sported a winged keel, one of several design-led innovations by Ben Lexcen that gave an edge. But the key was in the hardened sailing team, led by Bertrand, that maintained an unshakeable belief. 

They topped the round robin series, then won the Louis Vuitton Cup 4-1 over Britain’s Victory. 

Facing Conner’s Liberty, Australia II lost three of the first four races, two due to gear failure, and looked doomed. But they won the next two, forcing the first decider in Cup history. 

It was a stunner. Conner was ahead until the penultimate leg, when his failure to cover the Australians, who picked the correct wind shifts, took them ahead. In the final leg Conner threw the kitchen sink — with nearly 50 tacks — but Australia II held strong and won by 41 seconds.

This was redemption for New Zealand as a sailing nation. 

After the desperate disappointment of 2013, the fine margins of 2007 and the disaster of 2003, the emphatic victory in Bermuda was a wonderful triumph. 

It was made sweeter by beating Spithill, and his mega-funded Oracle team. 

Team New Zealand had been revitalised with new blood, principally Burling and Blair Tuke, and the young sailors seemed free of the baggage of past failures, although they were well led by Glenn Ashby. 

Bermuda was a far from ideal location, but the 50-feet foiling catamarans were engineering marvels, and wonderful to watch as they flew around the course. 

Team New Zealand had learned from San Francisco and didn’t reveal their full capabilities until it mattered, holding some things back in the preliminaries. 

But they mastered the art of foiling ahead of everyone else — becoming the first team to complete a race “in the air” and also bounced back from the frightening pitch pole moment against Ben Ainslie Racing in the semifinals, thanks to the outstanding work of the shore crew. 

The 26-year-old Burling exhibited the mastery of a veteran during the Cup match, which was won 7-1, as he consistently outwitted Spithill. 

“I don’t think we’d be here without the heartache of San Francisco,” said Burling, who was sailing in his first America’s Cup campaign, after being part of the back-up crew in 2013. 

“It’s unreal, this is exactly what we came here to do. I’m just on top of the world. It’s been three years of hard work, probably 100 people working at one time at this goal.”