18ft Skiffs: John 'Woody' Winning - 50 years of top level 18ft Skiff racing
by Frank Quealey 7 Oct 2025 06:37 BST
Fifty years ago, the 23-year-old Interdominion 12ft skiff champion John 'Woody' Winning joined the 18 footers class in a new skiff which was built by Bob McLeod and raced as Travelodge with the NSW 18 Footers League club's 1975-76 season fleet on Sydney Harbour.
John had sailed a few 18 footer races as a crew member and was well known as an up-and-coming champion of the future, but few could have realised that this 'rookie' 18s skipper would go on to become one of the three greatest influencers on the 134-year-old iconic Australian sport.
Mark Foy was the first of the three. He was founder of the 18s in 1892 and turned sailing in Australia from a competitor-driven 'pastime' into a high profile spectator sport - similar to the various football codes.
Next came James Joseph Giltinan, the man who introduced Rugby League to Australia in 1908. He was responsible for the formation of the NSW 18 Footers League in the early 1930s and introduced the World 18 footer Championship to Sydney Harbour in 1938.
John 'Woody' Winning's introduction to the 18s was successful but the competition in the 1975-76 season Australian fleet was so strong that he just missed selection in the six-boat team to represent at the 1976 worlds in Sydney.
It was the only time he would miss selection and John would later go on to become Giltinan World champion in 2000 (AMP Centrepoint) as well as runner-up twice (Pacific Harbour Fiji in 1980 and Yandoo in 1981) to the incredible Color 7 team of Iain Murray, Andrew Buckland and Don Buckley.
'Woody' and his team was also runner-up three times to Color 7 in successive Australian titles.
When the 15-year long Travelodge Hotels group sponsorship ended in 1980, another great long-term sponsor, Mr Patrick Corrigan, AM was quick to join forces with 'Woody' under the Mitchell Cotts banner and the pair contested three world championship regattas between 1982 and 1984.
Following one season with Flora Margarine-2MMM in the 1984-85 season, 'Woody' took time off from full-time 18ft skiff racing to concentrate on the family's Winning Appliances business as well as establishing his family with the births of son John 'Herman' and daughter Jamie.
During this period, John was also President of the NSW 18 Footers League in 1984 and 1985.
With the family established and the business moving forward successfully, 'Woody' returned to the then-known Australian 18 Footers League and raced the 1995-96 season with a self-sponsored skiff, named Yandoo, under the famous red and blue oval colour patch of the 7th Field Artillery Regiment.
The 18s had gone through a difficult time during the late 1980s-mid 1990s and needed an individual with the skill to steer the class back to its former success.
His return marked one of tremendous good-fortune for both the sport and the League as John 'Woody' Winning has been at the fore-front of every area associated with the sport and the licensed club over the subsequent 30 years.
John's return to racing soon saw him reach the pinnacle of his success when he led the AMP Centrepoint team (Euan McNicol and Anthony 'Jack' Young) to victory at both the 2000 JJ Giltinan World Championship and Australian Championship on Sydney Harbour.
The 18s were progressing rapidly under the newly-introduced one-design hull with international events being staged in Europe, USA and New Zealand and John soon showed his undoubted ability by winning several championships in each of the three areas.
He won three European championships (2001, 2004 and 2011), the Mark Foy Trophy at Sonderborg, Denmark in 2011, the San Francisco International Championship in 2004 and the ANZAC Regatta at Auckland in 2010.
'Woody' also recalls, in 1982 the 18s went to Lake Tahoe after a planned California regatta, and he also became the High Sierra 18 footer champion.
John resumed the role of President of the Australian 18 Footers League in 2004, and his DNA can be found on every area of the sport; he is responsible for its present stability and growth.
Throughout the period of his Giltinan, Australian and international championship success of the 2000s, he has been a central part of the League's racing program for the full 21 year term of his presidency, and together with his family's initiatives, and financial support, has been a significant part of the League's success.
John and his wife Kerrie, together with the late Bob 'Killo' Killick, were the original trio who had the vision of presenting 18ft skiff racing to the world, and funded their idea. The result is that every 18ft skiff race on Sydney Harbour is now a very professional livestream production from the centre of the race track to the world.
The Winning Group, the family business name, has also been the major financial backer for the JJ Giltinan World Championship since 2007.
Former Australian 18 footer champion and class historian, John 'Steamer' Stanley is full of the highest praise for Woody: "John Winning puts far more back into the sport than he takes out of it. He is extremely generous with his time and money, and is always prepared to help fellow sailors or anyone who needs it."
He also added how much 'Woody' appreciates the history of the 18s: "John and I went for a sail on a replica of Aberdare, and we were both hooked on the challenge of sailing on such a boat so he had a replica built of Australia I, the 1946-1947 Australian Champion, on which his father and uncle were in the champion crew."
"It was the start of a rebuilding program (Historical 18s) to preserve and recreate the rich 18 footer history. As usual, he was prepared to back his belief with his own cash."
Incredibly, for around 24 years 'Woody' sailed a Historical 18 every Saturday at the Sydney Flying Squadron and backed up the following day to sail a modern skiff at the League every Sunday during an entire Australian season.
'Woody' and 'Steamer' were also at it again when they wanted to honour Mark Foy and his determination in the early 1900s to make the sport international, and came up with the concept of the Mark Foy Trophy competition which would be sailed at various locations around the world.
It is an international alternative to the JJ Giltinan World Championship, which is conducted annually on Sydney Harbour. The first Mark Foy Trophy regatta was sailed at Carnac, France in 2009.
Woody is dedicated to the preservation of the history of the iconic Australian 18 footer class and this dedication led to him having the original Mark Foy Interstate Challenge Cup (burned in a house fire) 'rebirthed' one hundred years after the first official winner, Westana in 1911-12.
The concept for the design of the rebirthed trophy began when 'Steamer' took a "bag full of molten metal" (presented by Nick Press on behalf of the Press family) to WJ Sanders together with a design drawing of a 1940s 18 footer by Alf Beashel, which now sits on the top of the new trophy.
The molten silver was refined and milled into sheet silver which was then used on the front feature plate and three large plates where the winners are listed. The outside of the boat, keel and rigging were highly polished and sits on two pieces of silver seaweed-type foliage.
An incredible contribution to the history of the 18s in Australia.
By 2023, John 'Woody' Winning was a 71-year-old competitor in one of the most demanding sailing classes on the planet, yet the indefatigable strength and ability of one of the sport's greats was still on display when 'Woody' skippered Yandoo to victory in the NSW 18ft skiff Championship.
Unfortunately, hip surgery has restricted Woody's ability to continue full-time skippering in the 18s at the moment, but he is definitely still considering some occasional appearances throughout the League's coming 2025-26 season on Sydney Harbour.
The ongoing success of Australia's iconic sport of 18ft Skiff Racing on Sydney Harbour, owes much to the incredible action and support of John 'Woody' Winning, the Winning family and the Winning family's business.
The Winning family sporting success story doesn't end with Woody.
John 'Herman' followed in Woody's footsteps as a skipper in the 18 footers and capped off a successful career when he led the self-sponsored Andoo team to victory in the 2023 Giltinan World Championship. That victory created another record for the family as they became the only father and son to win the coveted championship as skippers.
Daughter Jamie chose a different sporting pathway, equestrian, and has achieved similar success to her brother. She has competed at a high level throughout the world and in 2009 was named both 'NSW Young Rider of the Year' and 'Australian Young Rider of the Year'.
The Australian 18 Footers League's 2025-26 season commences this week (Sunday, October 12) when it conducts Race 1 of the Spring Championship for the Major Arthur Frizelle Trophy. The club's regular spectator ferry will follow the race, which will also be livestreamed by SailMedia.