| YEAR | YACHT | OWNER | COUNTRY |
| 1945 | Rani | Capt. John Illingworth R.N. | UK |
| 1946 | Christina | Bob Bull | NSW |
| 1947 | Westward | George Gibson | TAS |
| 1948 | Westward | George Gibson | TAS |
| 1949 | Trade Winds | Mervyn Davey | NSW |
| 1950 | Nerida | Colin Haselgrove | SA |
| 1951 | Struen Marie | Tom Williamson | NSW |
| 1952 | Ingrid | James Taylor | SA |
| 1953 | Ripple | Ron Hobson | NSW |
| 1954 | Solveig | Trygve & Magnus Halvorsen | NSW |
| 1955 | Moonbi | Hal Evans | NSW |
| 1956 | Solo | Vic Meyer | NSW |
| 1957 | Anitra V | Trygve & Magnus Halvorsen | NSW |
| 1958 | Siandra | Graham Newland | NSW |
| 1959 | Cherana | Russ Williams | NSW |
| 1960 | Siandra | Graham Newland | NSW |
| 1961 | Rival | Alby Burgin & N. Rundle | NSW |
| 1962 | Solo | Vic Meyer | NSW |
| 1963 | Freya | Trygve & Magnus Halvorsen | NSW |
| 1964 | Freya | Trygve & Magnus Halvorsen | NSW |
| 1965 | Freya | Trygve & Magnus Halvorsen | NSW |
| 1966 | Cadence | Jim Mason | NSW |
| 1967 | Rainbow II | Çhris Bouzaid | NZL |
| 1968 | Koomooloo | Denis O’Neil | NSW |
| 1969 | Morning Cloud | Edward Heath | UK |
| 1970 | Pacha | Robert Crichton-Brown | NSW |
| 1971 | Pathfinder | Brin Wilson | NZL |
| 1972 | America Eagle | Ted Turner | USA |
| 1973 | Ceil III | Bill Turnbill | Hong Kong |
| 1974 | Love & War | Peter Kurts | NSW |
| 1975 | Rampage | Peter Packer | NSW |
| 1976 | Piccolo | John Pickles | NSW |
| 1977 | Kialoa III | Jim Kilroy | USA |
| 1978 | Love & War | Peter Kurts | NSW |
| 1979 | Screw Loose | Bob Cumming | TAS |
| 1980 | New Zealand | NZ ROUND THE WORLD COMMITTEE | NZL |
| 1981 | Zues II | Jim Dunstan | NSW |
| 1982 | Scallywag | Ray Johnston | NSW |
| 1983 | Challenge | Lou Abrahams | VIC |
| 1984 | Indian Pacific | John Eyles & Gunter Heuchmer | NSW |
| 1985 | Sagacious | Gary Appleby | NSW |
| 1986 | Extension | Tony Dunn | NSW |
| 1987 | Sovereign | Bernard Lewis | NSW |
| 1988 | Illusion | Gino Knezic | VIC |
| 1989 | Ultimate Challenge | Lou Abrahams | VIC |
| 1990 | Sagacious V | Gary Appleby | NSW |
| 1991 IOR | Atara | John Storey , Harold Cudmore & Bill Sykes | IRE |
| 1991 IMS | She’s Apples | David Strong | NSW |
| 1992 IOR | Ragamuffin | Syd Fischer | NSW |
| 1992 IMS | Assassin | Robin Crawford | NSW |
| 1993 IOR | Wild Oats | Bruce Foye, Roger Hickman & Lance Peckman | NSW |
| 1993 IMS | Cuckoos Nest | Nigel Holman | NSW |
| 1994 | Raptor | Andreas Eichenauer | GER |
| 1995 | Terra Firma | Dean Wilson & Scott Carlile | VIC |
| 1996 | Ausmaid | Georgio Gjergja | VIC |
| 1997 | Beau Geste | Karl Kwok | Hong Kong |
| 1998 | AFR Midnight Rambler | Ed Psaltis & Bob Thomas | NSW |
| 1999 | Yendys | Geoff Ross | NSW |
| 2000 | SAP Ausmaid | Kevan Pearce | SA |
| 2001 | Bumblebee 5 | John Kahlbetzer | NSW |
| 2002 | Quest | Bob Steel | NSW |
| 2003 | First National | Michael Spies & Peter Johnston | NSW |
| 2004 | Aera | Nicholas Lykiadopulo | UK |
| 2005 | Wild Oats XI | Robert Oatley | NSW |
| 2006 | Love & War | Simon Kurts & Lindsay May | NSW |
| 2007 | Rosebud | Roger Sturgeon | USA |
| 2008 | Quest | Bob Steel | NSW |
| 2009 | Two True | Andrew Saies | SA |
| 2010 | Secret Mens Business 3.5 | Geoff Boettcher | SA |
| 2011 | Loki | Stephen Ainsworth | NSW |
| 2012 | Wild Oats XI | Robert Oatley | NSW |
| 2013 | Victoire | Darryl Hodgkinson | NSW |
| 2014 | Wild Rose | Roger Hickman | NSW |
| 2015 | Balance | Paul Clitheroe | NSW |
| 2016 | Giacomo | Jim Delegat | NZL |
| 2017 | Ichi Ban | Matt Allen | NSW |
| 2018 | Alive | Philip Turner | TAS |
| 2019 | Ichi Ban | Matt Allen | NSW |
| 2020 | Not conducted | | |
| 2021 | Ichi Ban | Matt Allen | NSW |
| 2022 | Celestial | Sam Haynes | NSW |
| 2023 | Alive | Philip Turner | TAS |
