Here is a list of all the prior regatta winners.
| Year | Venue/Host Fleet | Skipper | Crew | Boat | Home Fleet |
| 2024 | Hull YC, Hull, MA | Joe Berkeley | Linda Epstein | # 632 Retread | Hull # 14 |
| 2023 | Not Held | ||||
| 2022 | Inverness YC, Inverness, CA | Skip Allan | Sean Callagy | # 695 Smart Shoes | Inverness # 56 |
| 2021 | Hull YC, Hull MA | Joe Berkeley | Linda Epstein | # 632 Retread | Hull # 14 |
| 2020 | No Regatta Held (Covid19 Pandemic) | ||||
| 2019 | Inverness YC, Inverness, CA | Bill Barton | Chris Raney | # 695 Smart Shoes | Inverness # 56 |
| 2018 | Macatawa YC, Holland, MI | Joe Berkeley | Linda Epstein | # 632 Retread | Hull # 14 |
| 2017 | Sail Newport, Newport, RI | Joe Berkeley | Linda Epstein | # 632 Retread | Hull # 14 |
| 2016 | Inverness YC, Inverness, CA | Maggie Craig | Tom Craig | # 753 Pow Wow | Hull # 14 |
| 2015 | Macatawa YC, Holland, MI | Ben Craig | Tom Craig | # 753 Pow Wow | Hull # 14 |
| 2014 | Marblehead, MA | Joe Berkeley | Linda Epstein | # 632 Retread | Hull # 14 |
| 2013 | Inverness YC, Inverness, CA | Ross Weene | Eli Slater | # 608 Good Foot | Newport # 54 |
| 2012 | Gloucester, MA | John Huff | Mark Vanderberg | # 754 Glider | Chicago # 55 |
| 2011 | Macatawa YC, Holland, MI | John Huff | Mark VanderBerg | # 754 Glider | Chicago # 55 |
| 2010 | Macatawa YC, Holland, MI | John Huff | Mark Vanderberg | # 754 Glider | Chicago # 55 |
| 2009 | Kingston, ON | Mark Van Note | Josh Hill | # 239 Screaming Pelican | Newport # 54 |
| 2008 | Hull YC, Hull MA | Mark Van Note | Josh Hill | # 239 Screaming Pelican | Newport # 54 |
| 2007 | CORK, Kingston Ontario | Steve Clancy | John Murphy | # 4 Jolly Giant | Hull # 14 |
| 2006 | Newport, RI | Mark Van Note | Josh Hill | # 631 US Blues | Newport # 54 |
| 2005 | Macatawa Bay YC, Holland MI, #7 | Ann Craig | Tom Craig | # 753 Pow Wow | Hull # 14 |
| 2004 | CORK, Kingston Ontario | Ann Craig | Tom Craig | # 753 Pow Wow | Hull # 14 |
| 2003 | Chicago YC, Chicago IL, # 55 | Tim Botimer | # 300 Alter Ego | Bay City # 36 | |
| 2002 | Ft. Adams Sailing Ctr, Newport, RI # 54 | Anthony Katoun | Oakley Jones | # 714 Pigs | Newport # 54 |
| 2001 | Bay City YC, Bay City MI, # 36 | Rick Kraii | John Laundra | # 751 Kraii’s baby | Macatawa # 7 |
| 2000 | Falmouth YC, Falmouth, MA District 1 | Rick Kraii | J.D. Stone | # 751 Kraii’s Baby | Macatawa # 7 |
| 1999 | Cottage Park YC, Winthrop, MA District 1 | Rick Kraii | # 751 Kraii’s Baby | Macatawa # 7 | |
| 1998 | Macatawa Bay YC, Holland, MI # 7 | Rick Kraii | # 751 Kraii’s Baby | Macatawa # 7 | |
| 1997 | Ocean City YC, Ocean City, NJ # 10 | Mike Blanchard | John Murphy | # 239 Plan B | Hull # 14 |
| 1996 | Hingham YC, Hingham MA # 29 | Russell Robinson | Alan Robinson | # 543 Life Boat | Hingham # 29 |
| 1995 | Chicago YC, Chicago, IL, #55 | Russell Robinson | Alan Robinson | # 543 Life Boat | Hingham # 29 |
| 1994 | Hull YC, Hull MA, # 14 | Russell Robinson | Alan Robinson | # 543 Life Boat | Hingham # 29 |
| 1993 | Bay City YC, Bay City MI # 36 | Russell Robinson | Alan Robinson | # 543 Life Boat | Hingham # 29 |
| 1992 | Boston Harbor YC, Boston, MA # 17 | Joe Berkeley | Dave McGrath | # 632 Retread | Hull # 14 |
| 1991 | Ft. Adams Sailing Ctr, Newport, RI # 54 | Tom Craig | Wil Craig | # 271 Wild Thing | Hull # 14 |
| 1990 | Macatawa Bay YC, Holland, MI, # 7 | Al Bonzelaar | Larry Boer | # 695 Mind Bender | Macatawa # 7 |
| 1989 | Corinthian YC, Marblehead MA, # 1 | Dru Slattery | Jack Slattery | # 545 Flash | Marblehead # 1 |
| 1988 | Hingham YC, Hingham, MA # 29 & # 14 (Hull YC) | Bill Higgins | Bill Donald | # 720 Rachel | Boston Bay # 17 |
| 1987 | Macatawa Bay YC, Holland, MI, # 7 | Dru Slattery | Jack Slattery | # 545 I.T.Y.W.B.T. Stern | Marblehead # 1 |
| 1986 | Falmouth YC, Falmouth, MA, District 1 | Dru Sour | Jack Slattery | # 736 Smurfette | Marblehead # 1 |
| 1985 | Ft. Adams Sailing Ctr, Newport, RI # 54 | Brad White | Bob Slattery | # 245 Malihini | Marblehead # 1 |
| 1984 | Bay City YC, Bay City, MI # 36 | Steve Clancy | Jim Kilfoyle | # 4 Jolly Giant | Hull # 14 |
| 1983 | Hull YC, Hull MA # 14 | Rick Kraii | Shelly Swaney | # 266 Kraii’s Baby | Macatawa # 7 |
| 1982 | Macatawa Bay YC, Holland, MI, # 7 | Jack Slattery | Kurt Fleming | # 545 Jumpin’ Jack Flash | Hull # 14 |
| 1981 | Boston Harbor YC, Boston MA # 17 | Jack Slattery | Kurt Fleming | # 545 Jumpin’ Jack Flash | Hull # 14 |
| 1980 | Bay City YC, Bay City, MI # 36 | Jack Driscoll | Jim Kilfolyle | Cracker Jack # 740 | Boston Bay # 17 |
| 1979 | Pleon YC, Marblehead, MA # 1 | Mark O’Conner | Bob O’Connor | Dingo # 736 | Marblehead # 1 |
| 1978 | Not Held | ||||
| 1977 | Macatawa Bay YC, Holland, MI, # 7 | Platt Johnson | Dennis Dixon | # 240 Elendil | Edgartown # 34 |
| 1976 | Edgartown YC, Edgartown, M.V. MA # 34 | Jay Mosher | John Elliot | # 548 Cookie Monster | Narragansett Bay #23 |
| 1975 | Corinthian YC/Seattle YC, Seattle, WA # 19 | Chris Waddell | Scott Kindred | # 33 Get Lost | San Diego # 13 |
| 1974 | Ocean City YC, Ocean City, NJ # 10 | Mike Butler | Jim Frost | # 662 Nulani | San Diego # 13 |
| 1973 | Bay City YC, Bay City, MI # 36 | Platt Johnson | Dennis Dixon | # 240 Elendil | Edgartown # 34 |
| 1972 | Hull YC, Hull MA # 14 | Doug MacDonald | Russ Williams | # 679 Sorcerer | San Francisco # 18 |
| 1971 | Richmond YC, S.F Bay, CA # 26 | Nate Russell | Gordon Nash, Jr | # 675 Endeavor | San Francisco # 18 |
| 1970 | City Island YC/EastChester YC, EastChester, NY #43 | Mark O’Conner | Bob O’Connor | # 102 Dingo | Marblehead # 1 |
| 1969 | Macatawa Bay YC, Holland, MI, # 7 | Mike Cuddy | Len Upham, Jr | # 510 Colleen | Narragansett Bay #23 |
| 1968 | Bristol YC, Bristol, RI #23 | Dave Curtis | Ken Bassett | # 145 Yellow Submarine | Marblehead # 1 |
| 1967 | San Diego YC, San Diego, CA # 13 | Terry Ryan | Bob Eschwege | # 635 Snake Pit | San Diego # 13 |
| 1966 | Northport YC, Northport Bay, NY #47 | Chuck Rudinsky | # 175 Zephyr | Boston Bay # 17 | |
| 1965 | Sheridan Shores YC, Wilmette, IL # 4 | Ron Dougherty | John Nicols | # 446 Kanigo | San Diego # 13 |
| 1964 | New Bedford, YC, S.Dartmouth, MA # 39 | Dave Curtis | # 496 Black Magic | Marblehead # 1 | |
| 1963 | Corinthian YC, S.F. Bay, CA # 18,& 26 | Gordon Nash | # 331 Javelin | Richmond # 26 | |
| 1962 | Indian harbor YC, Greenwich, CT, # 37 | Al Frost, Jr | # 364 Lani | San Diego, # 13 | |
| 1961 | Bay City YC, Bay City, MI # 36 | Al Frost, Jr | # 364 Lani | San Diego # 13 | |
| 1960 | Corinthian YC, Marblehead MA, # 1 | Al Frost, Jr | # 364 Lani | San Diego # 13 | |
| 1959 | San Diego YC, San Diego, CA # 13 | Al Frost, Jr | # 364 Lani | San Diego # 13 | |
| 1958 | Larchmont YC, W.L.I.S. # 2 | Seth Corwin | # 512 Rosie | Hingham # 29 | |
| 1957 | Sheridan Shores YC, Wilmette, IL # 4 | Malcom MacNaught | # 600 Black Cow II | Hingham # 29 | |
| 1956 | Hingham YC, Hingham, MA # 29 & # 14 (Hull YC) | Malcom MacNaught | # 600 Black Cow II | Hingham # 29 | |
| 1955 | Ocean City YC, Ocean City, NJ # 10 | Glit Shields | # 249 Iris | W.L.I.S | |
| 1954 | Richmond YC, S.F Bay, CA # 26 | Stephen Chadwick, Jr | # 424 Wild Flag | Lake Washington | |
| 1953 | San Diego YC, San Diego, CA # 13 | Les Harlander | # 344 Hot Breath | San Francisco | |
| 1952 | Gull Lake YC, Richland, MI # 6 | Bob Mann | # 360 Robin Too | San Diego | |
| 1951 | Sue Island YC, Baltimore, MD, # 11 | Larry Conover, Jr | #503 Revenoc, Jr | W.L.I.S | |
| 1950 | Richmond YC, S.F Bay, CA # 26 | Les Harlander | Don Harlander | #334 Hot Breath | San Francisco |
| 1949 | American YC, Rye, NY # 2 | Warner Wilcox | #225 Interim | W.L.I.S | |
| 1948 | Sheridan Shores YC, Wilmette, IL # 4 | Donald W. Sholle | # 6 Ten to one | W.L.I.S | |
| 1947 | Eastern YC, Marblehead, MA # 1 | Roger Wilcox | #135 Morss | MIT | |
| 1946 | Larchmont YC, W.L.I.S. # 2 | Roger Wilcox | #135 Morss | MIT | |
| 1945 | Not held | ||||
| 1944 | Not Held | ||||
| 1943 | Not Held | ||||
| 1942 | Corinthian YC, Marblead, MA # 1 | Frank Scully | #106 Auk | Marblehead | |
| 1941 | Grosse Pointe YC, MI # 3 | George O’Day | # 10 Vincimus | Marblehead | |
| 1940 | |||||
| 1939 |