The rumours that have swirled around the sailing community for months, that there would once again be an Australian entrant to the America’s Cup, seem to have finally been confirmed.

According to an announcement sent to members of Sydney’s Royal Prince Edward Yacht Club (RPEYC), and reports from Australian media outlets, the club has formally entered the 38th America’s Cup, scheduled to take place in Naples, Italy, in 2027.

Team Australia

Details are still a little thin on the ground and we await official confirmation but it looks as though the challenge will be spearheaded by the Winning family, led by John ‘Woody’ Winning and John ‘Herman’ Winning Jr. The family are icons in the Australian sailing and business world; John Winning Jr. is the CEO of Winning Group (and Appliances Online) and a seasoned sailor who skippered the 100-footer Andoo Comanche to a line honours win in the 2022 Rolex Sydney Hobart Race.

Both son and father have also been at the forefront of the Sydney 18ft skiff scene for many years.

The Royal Prince Edward Yacht Club, based in Point Piper, Sydney, will serve as the challenging yacht club. In the letter to members seen by us Commodore Sven Runow says that the challenge is a ‘clear reflection of the strength of our Club’ and aims to place Australia back at the ‘forefront of the international stage.’

The team is expected to compete under the banner of ‘Team Australia’, reviving a name that carries significant weight in the competition’s history.

John Bertrand’s Australia II en route to historic victory in the 1983 America’s Cup. Photo: Adam Stoltman / Alamy

Australia in the America’s Cup

Australia’s relationship with the Cup is defined by one of the greatest upsets in sporting history, followed by a long, quiet absence.

The country’s first challenger for the Cup came in 1962 with the 12-Metre Gretel, the first challenger to win a race against the Americans in decades. Throughout the ’60s and ’70s, Australian syndicates (notably those led by Sir Frank Packer and later Alan Bond) were persistent challengers, though they again repeatedly fell short against the mighty New York Yacht Club.

The pinnacle of Australian sailing came in 1983. Representing the Royal Perth Yacht Club, John Bertrand’s Australia II – featuring a revolutionary (and top-secret) winged keel designed by Ben Lexcen – defeated the American defender, Dennis Connor’s Liberty.

The 4-3 series victory ended the longest winning streak in sports history (132 years). It remains a cultural touchstone in Australia, famous for Prime Minister Bob Hawke’s quote: “Any boss who sacks a worker for not turning up today is a bum.”

Australia hosted the defense in Fremantle in 1987 – often cited as one of the pinnacle AC regattas in history – but the trophy was won back by Dennis Conner and the Americans (inspiring the Hollywood movie Wind). Following that loss, Australian involvement began to wane as the costs of the competition skyrocketed.

It has been 25 years since a formal Australian challenge actually made it to the starting line of an America’s Cup, although Andoo Team Australia fielded AC40 entries in the Youth and Women’s America’s Cup in Barcelona in 2024.

The last official Australian challenge was the ‘Young Australia’ syndicate in the 2000 America’s Cup in Auckland. This may not have been a succesfull challenge but it did kickstart the illustrious America’s Cup career of then-young skipper, Jimmy Spithill.

Since then, while Australian sailors and designers have featured heavily in the winning teams of the USA, Switzerland, and New Zealand, but there has been no flag-bearing Australian team. However, Australian talent still sits at the very forefront of the professional racing scene and the continuing success of Tom Slingby’s Australian-flagged SailGP team will, presumably, not have gone unnoticed.

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