Miss Massachusetts America 2012
| Year | Name | Hometown | Age | Local Title |
| 2011 | Molly Whalen | Middleboro | 21 | Miss Taunton |
| 2010 | Loren Galler-Rabinowitz | Brookline | 24 | Miss Collegiate Area |
| 2009 | Amanda Kelly | Braintree | 23 | Miss Fall River |
| 2008 | Alicia Zitka | West Springfield | 22 | Miss Hampden County |
| 2007 | Valerie J Amaral | Acushnet | 22 | Miss North Shore |
| 2006 | Michaela Gagne | Fall River | 24 | Miss Southcoast |
| 2005 | Kristin Gauvin | Worcester | 23 | Miss Apponagansett Bay |
| 2004 | Erika Ebbel | Cambridge | 23 | Miss Apponagansett Bay |
| 2003 | Melissa Silva | Fall River | 23 | Miss Southern Massachusetts |
| 2002 | Melanie Correia | Acushnet | 22 | Miss Taunton |
| 2001 | Abbie Rabine | Wenham | 22 | Miss Southern Massachusetts/Freetown |
| 2000 | Michelle Neves | New Bedford | 23 | Miss Pioneer Valley |
| 1999 | April Thibeault | Boston | 21 | Miss North Shore |
| 1998 | Elizabeth Hancock | Cambridge | 20 | Miss Suffolk County |
| 1997 | Samira Zebian | Westfield | 20 | Miss Tri-Counties/North Shore |
| 1996 | Lori Flick | Boston | 24 | Miss Tri-Counties/North Shore |
| 1995 | Marcia Turner | Cambridge | 21 | Miss Tri-Counties/North Shore |
| 1994 | Sharon Lee | Somerville | 24 | Miss Tri-Counties/North Shore |
| 1993 | Ellen Fitzgerald | Saugus | 22 | Miss Bay State |
| 1992 | Lisa Desroches | New Bedford | 21 | Miss New Bedford |
| 1991 | Melissa Bloemker | East Boston | 20 | Miss Greater Boston |
| 1990 | Marissa Laakso | Randolph | 24 | Miss Bay State |
| 1989 | Janette Elman | Attleboro | 22 | Miss Greater Attleboro |
| 1988 | Diana Steckler | East Boston | 22 | Miss East Boston |
| 1987 | Aurelie McCarthy | East Boston | 24 | Miss East Boston |
| 1986 | Kathleen Callahan | Revere | 23 | Miss Boston |
| 1985 | Lisa Kleypas | Carlisle | 20 | Miss Tri-County |
| 1984 | Margaret O'Brien | Weymouth | 26 | Miss Cape Cod |
| 1983 | Holly Mayer | Brookline | 26 | Miss Merrimack Valley |
| 1982 | Lisa Scorgie | North Attleboro | 23 | Miss Attleboro |
| 1981 | Deborah Salois | North Andover | 19 | Miss Methuen |
| 1980 | Amy Linder | Lowell | 22 | Miss Methuen |
| 1979 | Lisa Matta | Brockton | 20 | Miss Boston |
| 1978 | Rowena Humphrey | Worthington | 20 | Miss Northern Berkshire |
| 1977 | Janice Ould | Boston | 25 | Miss Methuen |
| 1976 | Deborah Guastella | Methuen | 22 | Miss Merrimack Valley |
| 1975 | Cynthia Carpenter | Wayland | 22 | Miss Marlboro |
| 1974 | Susan Sadlier | Lowell | 22 | Miss Newburyport/Coast Guard |
| 1973 | Rena Walmsley | North Attleboro | 20 | Miss Attleboro |
| 1972 | Marie Semas | Taunton | 18 | Miss Taunton |
| 1971 | Deborah O'Brien | Foxboro | 22 | Miss Foxboro |
| 1970 | Diana Dohrmann | Boston | 21 | |
| 1969 | Georgina Hossfeld | Burlington | 22 | Miss Burlington |
| 1968 | Catherine Monroe | Lynnfield | 20 | Miss Woburn |
| 1967 | Maria Chafee | Woburn | 18 | Miss Waltham |
| 1966 | Carol Kennedy | Worcester | 19 | Miss Northboro |
| 1965 | Mabel Bendiksen | New Bedford | 18 | Miss New Bedford |
| 1964 | Kathleen Kenneally | Whitman | 21 | Miss Brockton |
| 1963 | Lila Saldani | Attleboro | Miss Attleboro | |
| 1962 | Karen Behn | North Dartmouth | 18 | Miss New Bedford |
| 1961 | Nona Smith | Fairhaven | 18 | Miss New Bedford |
| 1960 | Brenda Crovo | Reading | 20 | Miss Cambridge |
| 1959 | Sharon Faught | Holyoke | 21 | |
| 1958 | Patricia Nordling | Lexington | ||
| 1957 | Daly Hirsch | Boston | ||
| 1956 | Jewel Smerage | Boston | ||
| 1955 | Virginia Maffucci | Watertown | ||
| 1954 | Judith Drake | Fairhaven | ||
| 1953 | Lois Feldman | Natick | ||
| 1952 | Barbara Graves | Milton | ||
| 1951 | Mildred Almeida | New Bedford | ||
| 1950 | Britta Berg | Boston | ||
| 1949 | Gloria Curelli | Roslindale | ||
| 1948 | Barbara Laughton | Reading | ||
| Barbara McGrath | Boston | |||
| 1946 | Rae Nichols | Malden | ||
| Paula C. Jerome | Boston | |||
| 1945 | Ruth Thomas | Belmont | ||
| Claire Thibadeau | Boston | |||
| 1944 | Lucille Descoteau | Lowell | ||
| Paulina McKevitt | Boston | |||
| 1943 | Mary McAnulty | Roslindale | ||
| Helena Frances Mack | Boston | |||
| 1942 | Paula Bordman | Natick | ||
| 1941 | Betsy Taylor | Cambridge | ||
| 1940 | Polly Connors | Bedford | ||
| 1937 | Claire Nevulis | South Boston | ||
| 1936 | Marion Flynn | Norwood | ||
| 1935 | Rita Mae King | Leominster | ||
| Mary Stanley | Quincy | |||
| 1933 | Elsie Taylor | 17 |
