| 2005 | |||
 |
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| Kristin Gauvin | |||
| 2004 | 2003 | 2002 | 2001 |
 |
 |
 |
 |
| Erika Ebbel | Melissa Silva | Melanie Beth Correia | Abbie Lynne Rabine |
Miss Massachusetts Through The Years
| 2005 | |||
|
|
|||
| Kristin Gauvin | |||
| 2004 | 2003 | 2002 | 2001 |
|
|
|
|
|
| Erika Ebbel | Melissa Silva | Melanie Beth Correia | Abbie Lynne Rabine |
| 2000 | 1999 | 1998 | 1997 |
 |
 |
 |
|
| Michelle Ann Neves | April Thibeault | Elizabeth Emerson Hancock | Samira Zebian |
| 1996 | 1995 | 1994 | 1993 |
 |
 |
 |
 |
| Lori Flick | Marcia Turner | Sharon Eunjoo Lee | Ellen Fitzgerald |
| 1992 | 1991 | 1990 | 1989 |
 |
 |
 |
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| Lisa Desroches | Melissa Bloemker | Marissa Laakso | Janette Elman |
| 1988 | 1987 | 1986 | 1985 |
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 |
 |
 |
| Diana Steckler | Aurelie McCarthy | Kathleen Callahan | Lisa Kleypas |
| 1984 | 1983 | 1982 | 1981 |
 |
 |
 |
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| Margaret O'Brien | Holly Jan Mayer | Lisa Jean Scorgie | Deborah Salois |
| 1980 | 1979 | 1978 | 1977 |
 |
 |
 |
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| Amy Linder | Lisa Jean Matta | Rowena Humphrey | Janice Avery Ould |
| 1976 | 1975 | 1974 | 1973 |
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 |
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| Deborah Guastella | Cynthia Carpenter | Susan Sadlier | Rena Walmsley |
