Below is a table of winners of the Regatta throughout the years. The overall winners are in bold print. Please e-mail contact@portandstarboardyachtclub.org with additional information or edit suggestions.
| Date | Location | Winner Class 1 | Winner Class 2 | Winner Class3 | Link |
|---|---|---|---|---|---|
| 2017 7-29 | internal link | ||||
| 2016 | Pisces - Harry Fish, Jr. | ||||
| 2015 8-8 | Pisces - Harry Fish, Jr. | ||||
| 2014 | (No Race) | - | - | - | - |
| 2013 | Pisces - Harry Fish, Jr. | ||||
| 2012 | Pisces - Harry Fish, Jr. | internal link | |||
| 2011 8-6 | Chandler Bay | Dream II - Arthur Hill | Aegir - Bernie Sund | Pisces - Harry Fish, Jr. | |
| 2010 | |||||
| 2009 | |||||
| 2008 | |||||
| 2007 8-11 | Who - Stephen Woolsey & Starr Sweeney | Lola - John & Judy Bielecki | internal link | ||
| 2006 8-12 | Machias Bay | Pisces - Harry Fish, Jr. | internal link | ||
| 2005 | |||||
| 2004 | |||||
| 2003 | |||||
| 2002 | |||||
| 2001 8-12 | Machias Bay | Ariel - William Transue, Jr. | Esoteria - Mark Breyfogle | Zephyr - Harper Dean | |
| 2000 8-12 | Ariel - William Transue, Jr. | Blossom - John Bielecki | Pisces - Harry Fish, Jr. | ||
| 1999 8-7 | Machias Bay | Ariel - William Transue, Jr. | Io - William Transue, Sr. | Lady K - Mark Kaplan | |
| 1998 8-9 | Machias Bay | Yellow Peril - Ed Cates | - | - | |
| 1997 7-26 | Machias Bay | Yellow Peril - Ed Cates | Io - William Transue, Sr. | Spectrum - Sandy Wurmfeld | |
| 1996 8-3 | Machias Bay | Yellow Peril - Ed Cates | Kathy Ann - Bob elmer | Lady K - Mark Kaplan | |
| 1995 7-30 | Machias Bay | Yellow Peril - Ed Cates | Westwind - David Rier | Intrigue - Ted Naughton | |
| 1994 7-30 | Machias Bay | Ariel - William Transue, Jr. | Tina Marie - Jim Mayhew | - | |
| 1993 7-24 | Machias Bay | Ariel - Tom Transue | La Otra - Hans van der Shoot | Caritas - Ed Greaves | |
| 1992 7 | Machias Bay | Yellow Peril - Ed Cates | La Otra - Hans van der Shoot | Intrigue - Ted Naughton | |
| 1991 7 | Machias Bay | Yellow Peril - Ed Cates | La Otra - Hans van der Shoot | Morning Mist - George Arey | |
| 1990 7-28 | Machias Bay | Ariel - Tom Transue | Islander II - John Breyfogel | Morning Mist - George Arey | |
| 1989 7-22 | Machias Bay | Loonie Too - John Cushing | Sonett - Karl Larson | Advent - Ken Rich | |
| 1988 7-30 | Machias Bay | Ariel - Tom Transue | Sonett - Karl Larson | Magnet - Ted Naughton | |
| 1987 7-25 | Machias Bay | Ariel - Tom Transue | Io - William Transue, Sr. | Windswift - Jim Wells | |
| 1986 8-6 | Machias Bay | Elsewhere - William Transue, Sr. | Estoteria - John Breyfogle | Magnet - Ted Naughton | |
| 1985 7-20 | Machias Bay | Elsewhere - William Transue, Sr. | Sonett - Karl Larson | Pisces - Harry Fish, Jr. | |
| 1984 | Machias Bay | Estoteria - John Breyfogle | Pisces - Harry Fish, Jr. | ||
| 1983 | Machias Bay | Pisces - Harry Fish, Jr. | |||
| 1982 | Machias Bay | Ariel - John & Kit Transue | Io - Bill Transue, Jr. | Pisces - Harry Fish, Jr. | |
| 1981 | Machias Bay | Loon Legacy - Dana Urquhart | Sabrina - Wally Kurz | Pisces - Harry Fish, Jr. | |
| 1980 8-23 | Machias Bay | Loon Legacy - Dana Urquhart | Pisces - Harry Fish, Jr. | ||
| 1979 | Machias Bay | ||||
| 1978 | Machias Bay | Elsewhere - William Transue, Sr. | Deliverance - Art Totman | Windswift - Jim Wells | |
| 1977 | Machias Bay | Elsewhere - William Transue, Sr. | Deliverance - Art Totman | Pisces - Harry Fish, Jr. | |
| 1976 | Machias Bay | Elsewhere - William Transue, Sr. | Deliverance - Art Totman | Nuisance - Perry Sturges | |
| 1975 | Machias Bay | Pisces - Harry Fish, Jr. | |||
| 1974 | Machias Bay | Pisces - Harry Fish, Jr. | |||
| 1973 | Machias Bay | Simoon - Selwood | |||
| 1972 | Machias Bay | Simoon - Selwood | |||
| 1971 | Machias Bay | Quickstep - Art Totman | |||
| 1970 | (No Race, Art was in school) | - | - | - | |
| 1969 | Machias Bay | Weatherly - Batson | |||
| 1968 | Machias Bay | Yellow Jacket - Art Totman | - | - | |
| 1967 | Machias Bay | Elsewhere - William Transue, Jr. | |||