| FCIAC ALL COUNTY TENNIS TEAMS (BOYS) | ||||
| YEAR | East | West | Champion | Runner-Up |
| 1963 | New Canaan | |||
| 1964 | New Canaan | |||
| 1965 | New Canaan | |||
| 1966 | New Canaan | |||
| 1967 | New Canaan | |||
| 1968 | New Canaan | |||
| 1969 | New Canaan | |||
| 1970 | New Canaan | |||
| 1971 | STAPLES | Greenwich | STAPLES | |
| 1972 | New Canaan | |||
| 1973 | New Canaan | |||
| 1974 | New Canaan | Rippowam | New Canaan | |
| 1975 | Wilton | |||
| 1976 | New Canaan | Rippowam | New Canaan | |
| 1978 | STAPLES | Westhill | Westhill | |
| 1979 | STAPLES | Norwalk | Norwalk | |
| 1980 | STAPLES | Norwalk | Norwalk | |
| 1981 | New Canaan | Norwalk | New Canaan | |
| 1982 | STAPLES | Norwalk | STAPLES | |
| 1983 | Wilton | Norwalk | Wilton | |
| 1984 | STAPLES | Stamford | Stamford | |
| 1985 | Darien | Greenwich | Darien | |
| 1986 | New Canaan | Greenwich | New Canaan | Greenwich |
| 1987 | New Canaan | Greenwich | New Canaan | Greenwich |
| 1988 | New Canaan | Greenwich | New Canaan | Greenwich |
| 1989 | Darien | Stamford | Darien | Ridgefield |
| 1990 | STAPLES | Stamford | Stamford | |
| 1991 | Stamford | STAPLES | STAPLES | Stamford |
| 1992 | STAPLES | Greenwich | Greenwich | STAPLES |
| 1993 | New Canaan | Greenwich | Greenwich | New Canaan |
| 1994 | New Canaan | Greenwich | New Canaan | Greenwich |
| 1995 | New Canaan | Greenwich | New Canaan | Greenwich |
| 1996 | New Canaan | Greenwich | Greenwich | |
| 1997 | New Canaan | Greenwich | Greenwich | STAPLES |
| 1998 | New Canaan | Greenwich | Greenwich | Darien |
| 1999 | STAPLES | Greenwich | STAPLES | |
| 2000 | STAPLES | Farfield | STAPLES | Darien |
| 2001 | STAPLES | Fairfield | STAPLES/FF-Tie | |
| 2002 | New Canaan | Greenwich | Greenwich | Fairfield |
| 2003 | STAPLES | Greenwich | Greenwich | STAPLES |
| 2004 | STAPLES | Greenwich | Greenwich | STAPLES |
| 2005 | STAPLES | Greenwich | Greenwich | STAPLES |
| 2006 | STAPLES | Greenwich | Greenwich | STAPLES |
| 2007 | STAPLES/Ludl/Dar | Greenwich | Greenwich | Ludlowe |
| 2008 | STAPLES | Greenwich | Greenwich | STAPLES |
| 2009 | New Canaan | Greenwich | Greenwich | Wilton |
| 2010 | New Canaan | STAPLES | New Canaan | STAPLES |
| 2011 | New Canaan | STAPLES | Greenwich | STAPLES |
| 2012 | New Canaan | Greenwich | Greenwich | STAPLES |
| 2013 | Ludlowe | Greenwich | Greenwich | STAPLES |
| 2014 | Warde | STAPLES | STAPLES | Ridgefield |
| 2015 | New Canaan | STAPLES | STAPLES | Greenwich |
| 2016 | New Canaan | Greenwich | STAPLES | Greenwich |
| 2017 | New Canaan | STAPLES | STAPLES | New Canaan |
| 2018 | ??? | STAPLES | STAPLES | Greenwich |
| 2019 | ??? | ??? | Darien | STAPLES |
| 2020 | No | Season | due to | Covid-19 |
| 2021 | Darien | STAPLES | Darien | STAPLES |
Staples Wreckers Boys Tennis 