Miss Massachusetts 2021 Elizabeth Pierre	Miss Massachusetts 2019 Lyndsey Littlefield	Miss Massachusetts 2018 Gabriela Taveras
Miss Massachusetts 2017 Jillian Zucco	Miss Massachusetts 2016 Alissa Musto	Miss Massachusetts 2015 Meagan Fuller
Miss Massachusetts 2014 Lauren Kuhn	Miss Massachusetts 2013 Amanda Narciso	Miss Massachusetts 2012 Taylor Kinzler
Miss Massachusetts 2011 Molly Whalen	Miss Massachusetts 2010 Loren Galler Rabinowitz	Miss Massachusetts 2009 Amada Kelly
Miss Massachusetts - 2008 Alicia Zitka	Miss Massachusetts 2007 Valerie Jeanne Amaral	Miss Massachusetts 2006 Michaela Gagne
Miss Massachusetts 2005 Kristin Gauvin	Miss Massachusetts 2004 Erika Ebbel	Miss Massachusetts 2003 Melissa Silva
Miss Massachusetts 2002 Melanie Beth Correia	Miss Massachusetts 2001 Abbie Lynne Rabine	Miss Massachusetts 2000 Michelle Ann Neves