| Year/Club | Champion | Fleet |
| 1948 at Edgartown | Frances Wakeman
- #20 FIREFLY | Cohasset |
| 1949
at Marblehead | Ed Hills - #81 COMET | Cohasset |
| 1950 at Larchmont | Richard Becker - #164 PRIDE | WLIS |
| 1951 at Manchester | Richard Fisher
- #1 ET TU | Cohasset |
| 1952
at Hawaii | Jerry Sheeley - #134 CHIEF | Hawaii |
| 1953 at San Francisco | Jerry Sheeley - #151 HIGHLAND BRIGADE | Hawaii |
| 1954 at Quincy Bay | King Durant - #166 SWAMI | Cohasset |
| 1955 at Manchester | Donnie McNamara - #188 BANTRY | Marblehead |
| 1956 at WLIS | Richard DeCew - #130
RIP | Larchmont |
| 1957
at Eastern Point | Dick Sullivan - #39 TYPHOON | Cohasset |
| 1958 at Boston Bay | Ed Hills - #233 SONATA | Cohasset |
| 1959 at Falmouth | Mort Bromfield - #242 CHALLENGE | Boston Bay |
| 1960 at Milford | Bob James - #299 SKIDDOO | Cohasset |
| 1961 at Cohasset | Mort Bromfield
- #242 CHALLENGE | Boston Bay |
| 1962
at WLIS | Robert Young - #304 RUNNING BEAR | WLIS |
| 1963 at Muskegon | Bob James - #299 SKIDDOO | Cohasset |
| 1964 at Cohasset | George Littlejohn
#302 WAR DRUM | Cohasset |
| 1965
at Gull Lake | Joe Schoendorf, Jr. - #349 CHARMER | Milwaukee |
| 1966 at Scituate | Bob Booth - #274 VOLANTE | Cohasset |
| 1967 at Milwaukee | Malcolm Hughes - #335 COQUINA | Muskegon |
| 1968 at Falmouth | Jim Summers - #239 PIROUETTE | Falmouth |
| 1969 at Muskegon | Roger Anderson
- #247 WHITECAP | Muskegon |
| 1970
at Cohasset | Rick Howard - #392 MELTEMI | Marblehead |
| 1971 at Gull Lake | Sherm Poppen - #249 HELZA | Muskegon |
| 1972 at Cohasset | Franny Charles - #258 FANFARE | Hull |
| 1973 at Milwaukee | Sherm Poppen - #249 HELZA | Muskegon |
| 1974 at Winthrop | Arthur Burke
- #315 ENCORE | Hull |
| 1975
at Muskegon | Sherm Poppen - #249 HELZA | Muskegon |
| 1976 at Falmouth | Billy O'Connor - #300 SAXA | Hull |
| 1977 at Gull Lake | Bill & Jim
Klerk & Jim Green - #310 BENIGN | Gull Lake |
| 1978 at Cohasset | Ken Cook - #369 MAGIC DRAGON | Cohasset |
| 1979 at Gull Lake | Bill Klerk -
#310 BENIGN | Gull Lake |
| 1980
at Eastern Point | Doug MacGregor - #299 RUBADUBDUB | Hingham |
| 1981 at Gull Lake | Dave Hatfield - #419 RAZMATAZZ | Gull Lake |
| 1982 at Hingham | Walter & Peter Schuchard - #290 TAX | Hingham |
| 1984 at Falmouth | John Keane - #392 GEZGO | Cohasset |
| 1985 at Milwaukee | Scott Bruesewitz
- #402 SURPRISE | Milwaukee |
| 1986
at Hingham | Dick Callahan - #357 ENCORE | Hingham |
| 1987 at Muskegon | Jeff Putney - #421 SCREAMIN' TUNA | Milwaukee |
| 1988 at Eastern
Point | John Keane - #392 GEZGO | Cohasset |
| 1989 at Milwaukee | Jeff Putney - #421 SCREAMIN' TUNA | Milwaukee |
| 1990 at Eastern
Point | Jim Robinson - #441 STRING TRIO | Hingham |
| 1991 at Milwaukee | Mike Blackwood - #321 LITTLE DARLIN' | Milwaukee |
| 1992 at Marblehead | Fran Charles, Jr - #258 FANFARE | Cohasset |
| 1993 at Muskegon | Mike Blackwood - #397 FIREWOOD | Milwaukee |
| 1994 at Eastern Point | Jeffrey
Kent - #392 GEZGO | Hingham |
| 1995
at Gull Lake | Jeff Putney - #451 SCREAMIN' TUNA | Milwaukee |
| 1996 at Gloucester | Stuart Hebb
- #435 AGINCOURT | Cohasset |
| 1997,
1998 | no contest: no wind |
| 1999
at | Jeff Putney - #451 SCREAMIN' TUNA | Milwaukee |
| 2000 at Hingham | Dick Partridge
- #447 PEAR TREE TOO | Hingham |
| 2001 at Gull Lake | Scott Busesewitz - #440 SURPRISE | Milwaukee |
2002 not sailed
2003 at Milwaukee | Tim
Putney - #451 SCREAMIN' TUNA | Milwaukee |
| 2004 at Falmouth | Oakley Jones - # 446 PIG PEN | Falmouth |
| 2005 at Gull Lake | | |
| 2006 at Quincy Bay | Jim Robinson - #441 String Trio | Hingham |
| 2007 at Gull Lake | Jim Babel #461 - Bullet | Gull
Lake |
