| CIAC State Championships |
| 2021 Class LL |
| [2020 SEASON CANCELLED DUE to COVID-19] |
| 2019 Class LL |
| 2018 Class LL |
| 2017 Class LL |
| 2016 Class LL (Co-Champions) |
| 2014 Class LL |
| 2011 Class LL |
| 2008 Class L |
| 2006 Class L |
| 2005 Class L |
| 2004 Class L |
| 2003 Class L |
| 2001 Class L |
| 2000 Class L |
| 1999 Class L |
| 1998 Class MM |
| 1991 Class L |
| 1988 Class LL |
| 1984 Class LL |
| 1983 Class LL |
| 1982 Class LL |
| FCIAC Championships |
| [2020 SEASON CANCELLED DUE to COVID-19] |
| 2018 |
| 2017 |
| 2016 |
| 2015 |
| 2014 |
| 2001 |
| 2000 |
| 1999 |
| 1991 |
| 1982 |
| 1962 |
| Division Championships |
| 2021 |
| [2020 SEASON CANCELLED DUE to COVID-19] |
| 2018 |
| 2017 |
| 2015 |
| 2014 |
| 2011 |
| 2010 |
| 2008 |
| 2007 |
| 2006 |
| 2005 |
| 2004 |
| 2003 |
| 2002 |
| 2001 |
| 2000 |
| 1999 |
| 1998 |
| 1992 |
| 1991 |
| Undefeated Seasons |
| 2018 (21-0) |
| 2017 (21-0) |
| 2015 (21-0) |
| 2014 (21-0) |
| 2001 (23-0) |
| 2000 (24-0) |
| 1999 (28-0) |
Staples Wreckers Boys Tennis 