The Winning Group 18ft Skiff team has set the standard with its domination of the first two races of the NSW 18ft Skiff Championship, presently being sailed on Sydney Harbour, and has brought into focus the possibility of her skipper John Winning Jr. and his father John ‘Woody’ Winning becoming the first father-and-son JJ Giltinan (world) Championship-winning skippers in the 81-year history of the prestigious championship.

John ‘Woody’ Winning had been runner-up twice to the legendry Iain Murray, Color 7, in the late 1970s before finally taking the prestigious Giltinan (world) title with AMP Centrepoint in 2000.

John Winning Jr. (aka ‘Herman’) won the 2002 World 29er Championship with Euan McNicol, when the pair defeated another ‘gun’ team of Nathan Outteridge and Grant Rose on Sydney Harbour.

‘Herman’ joined the 18ft Skiff ranks in 2008 when he skippered a new skiff, sponsored by, an online company he formed as part of his family’s business, and with his team of Dave Ewings and Tim Austin, finished fourth in a 32-strong fleet of teams from New Zealand, USA, UK and Canada.

Under the pressures of business, when John Jr. stepped up to become CEO of the 113-year-old family business, which has grown to become the ‘Winning Group’ with around 1,000 employees, he retired from regular 18ft Skiff Racing.

He came back into the 18s to compete in the Australian 18 Footers League’s 2018-2019 Season and the 2019 JJ Giltinan (world) Championship, but the team’s outlook seems far more determined in 2019-2020.

With seven-times JJ Giltinan Championship-winning skipper Seve Jarvin on the sheet and six-times JJ-winning bowman and Team Oracle America’s Cup winner, Sam Newton on board, Winning Group is looking like an early favourite to tackle the dominance the Kiwis have had at the JJs for the past two years.

Ironically, ‘Herman’ will be contesting the 2020 JJs against his father and against the skiff sponsored by the company he formed,, which will be skippered by the class boat builder Brett Van Munster.

Defending NSW champion James Dorron and his team of Harry Bethwaite and Tim Westwood had a slow start to the season but have shown a big improvement over the past two weeks to be runner-up in both races in their Shaw and Partners Financial Services-sponsored skiff.

After the first two races of the five-race NSW Championship, Winning Group leads the 18-boat fleet with a perfect score of 2, followed by Shaw and Partners Financial Services on 4, on 8, The Oak Double Bay-4 Pines (Aron Everett) on 9, Rag & Famish Hotel (Bryce Edwards) on 11, Smeg (Micah Lane) 15, Yandoo (John Winning) 18, Noakes Blue (Yvette Heritage) 18, The Kitchen Maker-Caesarstone 18.

Race 3 of the NSW Championship will be sailed from the Australian 18 Footers League on Sunday.

Spectators can see all the teams while they are rigging, then follow the racing on board the club’s spectator ferry, which leaves Double Bay Wharf, alongside the rigging area, at 2pm.

Book online through the club’s website

The AeroMedia Live Broadcast team will also be out on Sydney Harbour to capture all the action for those who can’t make it onto the water.

The livestreaming is available by going to and clicking on the ’18 Footers TV’ link.

As well as watching the livestreaming coverage, you can also follow all the club’s racing throughout the entire 2019-2020 Racing Season:

Club Website

Twitter @18skiff

Instagram @18skiff

Facebook International 18Ft Skiff