Sponsors
| Year | Boat Name | Boat # | Skipper | Crew | Regatta Location |
| 2024 | Where the bloody hell are you | 3880 | Craig Rainey | Ian Rainey | Gippsland Lakes YC |
| 2023 | Flying Flamingo | 3890 | Lewis Davies | John Radnell | Apollo Bay SC |
| 2022 | Oxfactor | 3905 | Michael Oxley | Gary Cameron | Gippsland Lakes YC |
| 2020 | Not Sailed due to COVID-19 | Lock | Down | ||
| 2019 | Where the bloody hell are you | 3880 | Craig Rainey | Ian Rainey | Cairn Curran SC |
| 2018 | 2C’s | 4006 | Chris Jackson | Chris Schwarz | Davey's Bay YC |
| 2017 | Ten Pound Note | 3611 | Peter Milne | Trevor Williams | Gippsland Lakes YC |
| 2016 | Never Say Die | 4007 | Sue Thompson | Cameron Taylor | Mordialloc SC |
| 2015 | Lapse of Reality | 3968 | Peter Milne | Phillip Dubbin | Davey's Bay YC |
| 2014 | I'd swap this for a Bundy | 3880 | Brent Frankcombe | Ben Jones | Cairn Curran SC |
| 2013 | I'd swap this for a Bundy | 3880 | Adam Hawkins | Ben Jones | Gippsland Lakes YC |
| 2012 | I'd swap this for a Bundy | 3880 | Adam Hawkins | Ben Jones | Mordialloc SC |
| 2011 | Aussie Falcon | 3930 | Dale Collings | Glenn Scheen | Cairn Curran SC |
| 2010 | Visit to Ward 11A | 3311 | Matt Owen | Andrew Reed | Gippsland Lakes YC |
| 2009 | FIZZ | 3661 | Gavin Dagley | Glen Gibson | |
| 2008 | I'd swap this for a Bundy | 3881 | Adam Hawkins | Brent Frankcombe | |
| 2007 | Where the bloody hell are you | 3880 | Craig Rainey | Ian Rainey | |
| 2006 | Grin & Bare It | 3663 | Craig Rainey | Ian Rainey | Mordialloc SC |
| 2005 | Relience Ffenty Ffun | 3836 | W. Shand | David Parish | |
| 2004 | Grin & Bare It | 3663 | Craig Rainey | Ian Rainey | |
| 2003 | Grin & Bare It | 3663 | Craig Rainey | Ian Rainey | |
| 2002 | ED | Peter Gale | Chris Mason | ||
| 2001 | Watches of Switzweland | 3723 | Peter Gale | Chris Mason | |
| 2000 | Gun-N-Dunnit | 3620 | David Meldrum | M. Brown | |
| 1999 | Gun-N-Dunnit | 3620 | David Meldrum | M. Brown | |
| 1998 | Think Big | 3257 | Craig Rainey | Ian Rainey | |
| 1997 | Think Big | 3257 | Craig Rainey | Ian Rainey | |
| 1996 | Molly O | 3099 | M. Bulka | H. Proctor | |
| 1995 | Ffidelity | 3238 | A. Jensen | R. Hunter | |
| 1994 | Gunnadoo | 2755 | David Meldrum | M. Brown | |
| 1993 | Ruffa Gruffa | 3313 | J. Thompson | M. Richie | |
| 1992 | Ruffa Gruffa | 3313 | J. Thompson | M. Richie | |
| 1991 | Ffidelity | 3238 | J. Thompson | M. Richie | Royal Geelong YC |
| 1990 | Relience 60 over 5 | 3257 | W. Shand | D. Sanders | Sandringham YC |
| 1989 | Tradesmans Entrance | 3062 | Craig Rainey | S. Walsh | Gippsland Lakes YC |
| 1988 | Tradesmans Entrance | 3062 | Craig Rainey | S. Walsh | Davey's Bay YC |
| 1987 | Glass Slipper | 2834 | Glenn Collings | John Collings | Gippsland Lakes YC |
| 1986 | W. Beaut | 2824 | Glenn Coulton | Paul Alford | Mornington YC |
| 1985 | Tradesmans Entrance | 3062 | Craig Rainey | S. Walsh | Gippsland Lakes YC |
| 1984 | Here we go again | 2906 | Glenn Coulton | M. Holmes | Davey's Bay YC |
| 1983 | Relience VII | 2908 | W. Shand | H. Shand | Portland YC |
| 1982 | Scandel | 2247 | Glenn Coulton | C. Wilson | Davey's Bay YC |
| 1981 | Waterbird | 1202 | Rod Dalgleish | Jim Howell | Port Melbourne YC |
| 1980 | Cheeky Chic | 2403 | G. Gadsden | . | Bendigo YC |
| 1979 | Shemozzle | 2250 | C. Villa | . | Mornington YC |
| 1978 | Relience VI | 1677 | W. Shand | H. Shand | Royal Geelong YC |
| 1977 | Relience III | 1663 | W. Shand | H. Shand | Mornington YC |
| 1976 | Relience III | 1663 | W. Shand | H. Shand | Davey's Bay YC |
| 1975 | Relience III | 1663 | W. Shand | H. Shand | Mornington YC |
| 1974 | Innisfree | 1410 | P. McAuley | . | Royal Geelong YC |
| 1973 | Flight III | 946 | J.A. Calvert-Jones | . | Davey's Bay YC |
| 1972 | Relience II | 961 | W. Shand | H. Shand | Royal Geelong YC |
| 1971 | Relience II | 961 | W. Shand | H. Shand | Gippsland Lakes YC |
| 1970 | Relience II | 961 | W. Shand | H. Shand | Davey's Bay YC |
| 1969 | Relience II | 961 | W. Shand | H. Shand | Mornington YC |
| 1968 | Relience | 761 | W. Shand | H. Shand | Royal Geelong YC |
| 1967 | Ffidelity | 868 | R.T Boynton | L. Syme | Sandringham YC |
| 1966 | Relience | 761 | W. Shand | H. Shand | Mornington YC |
| 1965 | Relience | 761 | W. Shand | H. Shand | Mornington YC |
| 1964 | Ffalanger | 550 | W. Shand | L. Shand | Gippsland Lakes YC |
| 1963 | Sea Weed | 575 | E. Maizey | . | Gippsland Lakes YC |
| Year | Boat Name | Skipper | Crew |
| 2024 | Ffidelity | Lewis Davies | Shane Davies |
| 2023 | Clockwork VII | Mick Swales | Kevin Buschert |
| 2022 | Molly O | John Foley | Noelene Foley |
| 2020 | Not Sailed due to COVID-19 Lockdown | ||
| 2019 | Relience 60/5+1 | Craig Conn | Michael McCartney |
| 2018 | Clockwork VII | Mick Swales | Kevin Buschert |
| 2017 | Ffidelity | Lewis Davies | John Radnell |
| 2016 | Fformidable | Lewis Davies | John Radnell |
| 2015 | Flying Boat | John Radnell | Robert Radnell |
| 2014 | Fformidable | Lewis Davies | J. Owen-Smith |
| 2013 | Ffirsty | Andrew Peck | Errol Peck |
| 2012 | Ffidelity | Lewis Davies | Shane Davies |
| 2011 | F 'n F | Jim Callahan | B. Hancock |
| 2010 | Visit to Ward 11A | Matt Owen | Andrew Reed |
| 2009 | |||
| 2008 |
| Year | Boat Name | Skipper | Crew |
| 2024 | April Dancer | Bruce Johnson | Geraldine Lewin |
| 2023 | April Dancer | Bruce Johnson | Geraldine Lewin |
| 2022 | April Dancer | Bruce Johnson | Geraldine Lewin |
| 2020 | Not Sailed due to COVID-19 | Lockdown | |
| 2019 | Affrodite | Tim Cobb | Andrew Smith |
| 2018 | Affrodite | Tim Cobb | Chris Adams |
| 2017 | Affrodite | Tim Cobb | Andrew Smith |
| 2016 | Affrodite | Tim Cobb | Anton Tibbits |
| 2015 | No Classic Entries | ||
| 2014 | The Gremlin | James Frecheville | Ben Frecheville |
| 2013 | Iffy | Phil Parish | Matthew Richards |
| 2012 | The Gremlin | James Frecheville | Ben Frecheville |
| 2011 | Affrodite | Regan Burdon-Bear | Les Kearney |
| 2010 | Affrodite | Regan Burdon-Bear | Les Kearney |
| 2009 | Black Pearl | Lisa Deppeler | I. Lane |
| 2008 | In The Pink | M. Deppeler | A. Millar |
| 2007 | In The Pink | A. Millar | T. Harrison |
| 2006 | Iffy | Clive Arnold | A. Maclean |
| 2005 | Iffy | Clive Arnold | G. Giles |
| 2004 | Euffamism | Les Kearney | A. Harman |
| 2003 | In The Pink | Regan Burdon-Bear | A. Miller |
| 2002 | Slippery When Wet | R. Muller | J. Dusting |
| 2001 | Town Bike | G. Ginnivan | D. Hocking |
| 2000 | |||
| 1999 |
|
Year |
Winning Club Name |
Boat Names X 3 |
Regatta Location |
| 2024 | Davey's Bay YC |
Freshwater |
Sailed at GLYC |
| 2023 | Davey's Bay YC |
Flying Flamingo |
Sailed at Apollo Bay SC |
| 2022 | Davey's Bay YC |
Oxfactor |
Sailed at GLYC |
|
2021 |
Davey's Bay YC | The Flying Flamingo Oxfactor Aussie Falcon |
Sailed at DBYC |
|
|
|||
|
2019 |
Davey's Bay YC |
Snafu |
Sailed at CCSC |
|
2018 |
Davey's Bay YC |
2C's |
Sailed at DBYC |
|
2017 |
Gippsland Lakes YC |
Ten Pound Notes |
Sailed at GLYC |
|
2016 |
Mordialloc SC |
Cool Change |
Sailed at MSC |
|
2015 |
Mordialloc SC |
Lapse of Reality |
Sailed at DBYC |
|
2014 |
Mordialloc SC |
I'd swap this for a Bundy Aussie Falcon |
Sailed at CCSC |