The Mary Kay Smith Trophy
First awarded in 1999 by the North Stamford Exchange Club, this trophy is presented to the Stamford high school city championship softball team.
Mary Kay Smith pioneered the female athletic programs at Stamford Catholic High School and she had multiple State Championship titles in Softball. “MK” was inducted into the FCIAC Hall of Fame in 2000.
| 2015 | Westhill High School |
| 2014 | Stamford High School |
| 2013 | Westhill High School |
| 2012 | Westhill High School |
| 2011 | Westhill High School |
| 2010 | Westhill High School |
| 2009 | Stamford High School |
| 2008 | Westhill High School |
| 2007 | |
| 2006 | Stamford High School |
| 2005 | Stamford High School |
| 2004 | Stamford High School |
| 2003 | Westhill High School |
| 2002 | Stamford High School |
| 2001 | Stamford High School |
| 2000 | Stamford High School |
| 1999 | Westhill High School |