| Midget Champ, Runner Up |
Junior Champ, Runner Up | Senior Champ, Runner Up |
1985 | NA | NA | NA |
| NA | NA | Innis Arden |
|
1986 | NA | NA | NA |
| NA | NA | NA |
|
1987 | NA | NA | NA |
| NA | NA | NA |
|
1988 | Rocky Point Club | Tokeneke Club | Burning Tree Country Club |
| Roxbury Swim Club | Weston Field Club | Rocky Point Club |
|
1989 | Roxbury Swim Club | Rocky Point Club | Rocky Point Club |
| Rocky Point Club | Roxbury Swim Club | Riverside Yacht Club |
|
1990 | Roxbury Swim Club | Roxbury Swim Club | Rocky Point Club |
| Greenwich CC/ Stanwich | Rocky Point Club | Riverside Yacht Club |
|
1991 | Greenwich CC/ Stanwich | Rocky Point Club | Rocky Point Club |
| Roxbury Swim Club | Roxbury Swim Club | Riverside Yacht Club |
|
1992 | Milbrook Club | Rocky Point Club | Rocky Point Club |
| Roxbury Swim Club | Roxbury Swim Club | Rocky Point Club B |
|
1993 | Belle Haven Club | Roxbury Swim Club | NA |
| Innis Arden Club | New Canaan Field Club | NA |
|
1994 | Roxbury Swim Club | Burning Tree Country Club | Rocky Point Club |
| Belle Haven Club | Roxbury Swim Club | Burning Tree Country Club |
|
1995 | Burning Tree Country Club | Rocky Point Club | Rocky Point Club |
| Greenwich CC/ Stanwich | Burning Tree Country Club | Roxbury Swim Club |
|
1996 | Greenwich CC/ Stanwich | Burning Tree Country Club | Roxbury Swim Club |
| Burning Tree Country Club | Belle Haven Club | Burning Tree Country Club |
|
1997 | Riverside Yacht Club | Innis Arden Club | Burning Tree Country Club |
| Greenwich CC/ Stanwich | Roxbury Swim Club | Riverside Yacht Club |
|
1999 | Burning Tree Country Club | Burning Tree Country Club | Innis Arden Club |
| Rocky Point Club | Rocky Point Club | Rocky Point Club |
|
2000 | Innis Arden Club | Rocky Point Club | Innis Arden Club |
| Lake Club | New Canaan Field Club | Rocky Point Club |
|
2001 | Roxbury Swim Club | Burning Tree Country Club | Innis Arden Club |
| Middlesex Club | Rocky Point Club | Rocky Point Club |
|
2002 | Rocky Point Club | Rocky Point Club | Rocky Point Club |
| Roxbury Swim Club | Innis Arden Club | Burning Tree Country Club |
|
2003 | Rocky Point Club | Roxbury Swim Club | Burning Tree Country Club |
| Greenwich Country Club | Rocky Point Club | Rocky Point Club |
|
2004 | Rocky Point Club | Rocky Point Club | Rocky Point Club |
| Innis Arden Club | Roxbury Swim Club | New Canaan Field Club |
|
2005 | Rocky Point Club | Rocky Point Club | Burning Tree/Milbrook |
| Innis Arden Club | Burning Tree Country Club | Rocky Point Club |
|
2005 "B" | Tokeneke Club | Rocky Point Club | No Senior "B" Tournament |
| Middlesex Club | Middlesex Club | |
|
2006 | Innis Arden Club | Rocky Point Club | Rocky Point Club |
| New Canaan Field Club | Innis Arden Club | Roxbury Swim Club |
|
2006 "B" | Tokeneke Club | Middlesex Club | No Senior "B" Tournament |
| Middlesex Club | Country Club of Darien | |
|
2007 | Riverside Yacht Club | Innis Arden Club | Roxbury Swim Club |
| Rocky Point Club | Rocky Point Club | New Canaan Field Club |
|
2007 "B" | Tokeneke Club | Middlesex Club | No Senior "B" Tournament |
| Middlesex Club | Lake Club | |
|
2008 Div 1 | Roxbury Swim Club | Rocky Point Club | Rocky Point Club |
| New Canaan Field Club | Innis Arden Club | Roxbury Swim Club |
|
2008 Div 2 | Middlesex Club | Milbrook Club | Divs 1, 2, 3 & 4 are combined |
| Lake Club | Lake Club | |
|
2008 Div 3 | Long Ridge Club | Belle Haven Club | |
| Stamford Yacht Club | CC of New Canaan | |
|
2008 Div 4 | Divs 3 & 4 combined | Long Ridge Club | |
| | Waveny Pool | |
|