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These are the women who have previously held the title Miss Greater Worcester/ Miss Worcester County.

2010-Grace Pusavat*

2009-Jillian Lawton

3rd Runner Up

Miss Vermont 2009

2008- Laura Hall

2007-Alana Megna

2006-Lauren Mangano

2005-Jaclyn Mullavey*

3rd Runner Up

Interview Award

Miss Maine 2007

2004-Tara Allain

Most Talented Non-Finalist

Miss Massachusetts 2005

2003-Kristin Gauvin

Top 10 Semi-Finalist

Preliminary Swimsuit Winner

MAO Academic Award

2002- Michelle Santora

Most Talented Non-Finalist

2001-Sandra Lee Riel

Top 8 Semi-Finalist

2000-Katie Tokarz

1999-Jennifer Gibson

Most Talented Non-Finalist

1998-Jennifer Roy

Top 10 Semi-Finalist

* Indicates that the titleholder did not hail from the Greater Worcester Area. The Miss America Scholarship Organization requires that all local competitions have a minimum of 4 contestants per title awarded, when there are not at least 4 contestants competing for the title of Miss Greater Worcester/Miss Worcester County the pageant must "open" the competition to all eligable women in the state of Massachusetts to ensure that the title can be awarded at all. While the Miss Greater Worcester Scholarship Organization aims to recognize young women who hail directly from the Greater Worcester area lack of contestants may sometimes require that the title be made "open" to all interested women in the state of Massachusetts.

**The title of Miss Worcester County was awarded consecutively from 1998-2008, due to issues with Miss America Local Pageant rules related to the naming of a new executive director, the Worcester representitive's title name was changed to Miss Greater Worcester in 2009.