| Year | Sport | Class | Champion | Runnerup | Score | Link |
| 2023 | Golf (Boys) | Open | Boys: Bradley Sawka Girls: Laniah Moffett | Boys: Jack Wise Girls: Aoife Devaney | Boys: 71 Girls: 75 | |
| Golf (Boys) | Fall-I | Fairfield Prep | Glastonbury | 287 | |
| Golf (Boys) | Fall-II | Pomperaug | St. Joseph | 334 | |
| Golf (Boys) | Girls-I | Greenwich | New Canaan | 337 | |
| Golf (Boys) | Girls-II | Berlin | St. Paul Catholic | 337 | |
| Golf (Boys) | Spring-I | Cheshire | Bristol Central | 316 | |
| Golf (Boys) | Spring-II | Daniel Hand | Killingly | 306 | |
| Golf (Boys) | Spring-III | Portland | East Catholic | 313 | |
| 2022 | Golf (Boys) | Girls-I | New Canaan | Greenwich | 324 | |
| Golf (Boys) | Girls-II | Berlin | St. Paul Catholic | 333 | |
| Golf (Boys) | I-Fall | Greenwich | Farmington | 297 | |
| Golf (Boys) | II-Fall | Pomperaug | St. Joesph | 319 | |
| Golf (Boys) | Spring-I | Fairfield Prep | Cheshire | 304 | |
| Golf (Boys) | Spring-II | RHAM | Ellington | 311 | |
| Golf (Boys) | Spring-III | Portland | St. Paul | 310 | |
| Golf (Boys) | Open | Boys: Andrew Beauton
Girls: Anna Lemcke & Libby Dunn | Boys: Bradley Sawka
Girls: Sydney Hidalgo | Boys: 70
Girls: 79 | |
| 2021 | Golf (Boys) | Fall-I | New Canaan | Glastonbury | 312 | |
| Golf (Boys) | Fall-II | St. Joseph | Berlin | 317 | |
| Golf (Boys) | Girls-I | Hall | New Canaan | 349 | |
| Golf (Boys) | Girls-II | Woodstock Academy | Berlin | 369 | |
| Golf (Boys) | I | Fairfield Prep | Conard | 296 | |
| Golf (Boys) | II | Daniel Hand | Pomperaug | 299 | |
| Golf (Boys) | III | St. Joseph | Lewis Mills | 329 | |
| Golf (Boys) | IV | Portland | Immaculate | 316 | |
| Golf (Boys) | Open | Boys: Brett Chodos
Girls: Libby Dunn | Boys: Bradley Sawka
Girls: Anna DeSanto | Boys: 69
Girls: 81 | |
| 2019 | Golf (Boys) | Girls | New Canaan | Greenwich | 320 | |
| Golf (Boys) | I | Greenwich | Darien | 301 | |
| Golf (Boys) | II | Daniel Hand | Avon | 308 | |
| Golf (Boys) | III | East Catholic | Killingly | 315 | |
| Golf (Boys) | IV | Immaculate | Northwest Catholic | 323 | |
| Golf (Boys) | Open | Alexander Gu | Alexander Aurora | Boys: 75 | |
| 2018 | Golf (Boys) | Girls | New Canaan | Fairfield Warde | (Won 3-hole playoff 54-55) | |
| Golf (Boys) | I | Greenwich | Darien | 293 | |
| Golf (Boys) | II | Avon | Berlin | 293 | |
| Golf (Boys) | III | Killingly | East Catholic | (Won 3-hole playoff 50-52) | |
| Golf (Boys) | IV | Portland | Immaculate | 325 | |
| Golf (Boys) | Open | Chris Fosdick | Tyler Hahn | 67 | |
| 2017 | Golf (Boys) | Girls | New Canaan | Fairfield Warde | 348 | |
| Golf (Boys) | I | Xavier | Greenwich | 301 | |
| Golf (Boys) | II | Avon | New Canaan | 299 | |
| Golf (Boys) | III | Suffield | Killingly | 297 | |
| Golf (Boys) | IV | Portland | Immaculate | 323 | |
| 2016 | Golf (Boys) | Girls | Greenwich | Danbury | 341 | |
| Golf (Boys) | I | Simsbury | Xavier | 300 (Won 3-hole playoff) | |
| Golf (Boys) | II | Joel Barlow | Berlin / Notre Dame-West Haven | 313 | |
| Golf (Boys) | III | Killingly | East Catholic | 310 | |
| Golf (Boys) | IV | Portland | Litchfield / Morgan | 306 | |
| 2015 | Golf (Boys) | Girls | Berlin | Greenwich | 346 | |
| Golf (Boys) | I | Ridgefield | Greenwich / Glastonbury / Darien | 313 | |
| Golf (Boys) | II | New Canaan | Notre Dame-West Haven | 315 | |
| Golf (Boys) | III | East Catholic | Suffield | 297 | |
| Golf (Boys) | IV | Morgan | Canton | 333 | |
| 2014 | Golf (Boys) | Girls | Greenwich | Berlin | 335 | |
| Golf (Boys) | I | Glastonbury | Greenwich | 303 | |
| Golf (Boys) | II | Notre Dame-West Haven / New Canaan | | 306 (Co-Champions) | |
| Golf (Boys) | III | East Catholic | Tolland | 311 | |
| Golf (Boys) | IV | Morgan | Northwest Catholic | 320 (Won 3-hole playoff 55-57) | |
| 2013 | Golf (Boys) | Girls | Berlin | Greenwich/Staples | 358 | |
| Golf (Boys) | I | Pomperaug | Simsbury | 303 | |
| Golf (Boys) | II | Daniel Hand | New Canaan | 299 | |
| Golf (Boys) | III | Holy Cross | Weston | 309 | |
| Golf (Boys) | IV | Morgan | Coventry | 327 | |
| 2012 | Golf (Boys) | Girls | Berlin | Farmington | 348 | |
| Golf (Boys) | I | Greenwich | Amity/Xavier | 299 | |
| Golf (Boys) | II | Daniel Hand | New Canaan | 313 | |
| Golf (Boys) | III | Lewis Mills | Weston | 326 | |
| Golf (Boys) | IV | Northwest Catholic | Old Saybrook | 313 | |
| 2011 | Golf (Boys) | Girls | Berlin | Darien | 375 | |
| Golf (Boys) | I | Ridgefield | Greenwich | 307 | |
| Golf (Boys) | II | New Canaan | Watertown | 304 | |
| Golf (Boys) | III | Wolcott | Lewis Mills | 310 | |
| Golf (Boys) | IV | East Catholic | Northwest Catholic | 305 | |
| 2010 | Golf (Boys) | Girls | Farmington | Greenwich | 363 | |
| Golf (Boys) | I | Staples | Farmington | 300 | |
| Golf (Boys) | II | New Canaan | Avon | 298 | |
| Golf (Boys) | III | East Catholic | Granby Memorial | 307 | |
| Golf (Boys) | IV | Northwest Catholic | Canton | 314 | |
| 2009 | Golf (Boys) | Girls | Weston | Farmington | 375 | |
| Golf (Boys) | I | Staples | Simsbury | 297 | |
| Golf (Boys) | II | New Canaan | Berlin | 298 | |
| Golf (Boys) | III | Weston | Suffield | 307 | |
| Golf (Boys) | IV | Trinity Catholic | St. Paul Catholic/Northwest Catholic | 330 | |
| 2008 | Golf (Boys) | Girls | New Canaan | Staples | 371 | |
| Golf (Boys) | I | Simsbury | Greenwich/Staples | 298 | |
| Golf (Boys) | II | Berlin | Woodstock Academy | 300 | |
| Golf (Boys) | III | East Catholic | Weston | 319 | |
| Golf (Boys) | IV | Northwest Catholic | Putnam | 311 | |
| 2007 | Golf (Boys) | Girls | Staples | Simsbury | 385 | |
| Golf (Boys) | I | Simsbury | Southington | 307 | |
| Golf (Boys) | II | New Canaan | Berlin | 311 | |
| Golf (Boys) | III | Tolland | Lewis Mills | 310 | |
| Golf (Boys) | IV | Housatonic Valley | Northwest Catholic | 317 | |
| 2006 | Golf (Boys) | Girls | Staples | Berlin | 363 | |
| Golf (Boys) | I | Simsbury | Southington | 312 | |
| Golf (Boys) | II | New Canaan | Pomperaug | 305 | |
| Golf (Boys) | III | Tolland | Waterford | 313 | |
| Golf (Boys) | IV | Rocky Hill | Weston | 313 (Rocky Hill wins three hole playoff 49-52) | |
| 2005 | Golf (Boys) | Girls | Danbury | Mercy | 365 | |
| Golf (Boys) | I | Simsbury | Newington/New Britain | 294 | |
| Golf (Boys) | II | New Canaan | Wilton | 306 | |
| Golf (Boys) | III | Rocky Hill | Daniel Hand | 316 | |
| Golf (Boys) | IV | Weston | Housatonic Regional | 323 | |
| 2004 | Golf (Boys) | Girls | Danbury | Mercy | 391 | |
| Golf (Boys) | I | Greenwich | Newington | 313 | |
| Golf (Boys) | II | Berlin | New Canaan | 302 | |
| Golf (Boys) | III | Ellington | RHAM | 320 | |
| Golf (Boys) | IV | Tourtellotte | Hale Ray | 308 | |
| 2003 | Golf (Boys) | Girls | New Canaan | Fairfield | 375 | |
| Golf (Boys) | I | Hamden | Trumbull | 306 | |
| Golf (Boys) | II | Wilton | Berlin | 316 | |
| Golf (Boys) | III | New Canaan | Darien | 301 | |
| Golf (Boys) | IV | East Catholic | St. Paul | 307 | |
| 2002 | Golf (Boys) | I | Fairfield | Cheshire | 318 | |
| Golf (Boys) | II | Wilton | Berlin | 309 | |
| Golf (Boys) | III | New Canaan | Waterford/Woodstock Academy | 330 | |
| Golf (Boys) | IV | East Catholic | Granby Memorial | 324 | |
| 2001 | Golf (Boys) | I | Simsbury | Notre Dame-West Haven/Fairfield Prep | 324 (Won 3-hole playoff) | |
| Golf (Boys) | II | Berlin | Wethersfield | 302 | |
| Golf (Boys) | III | Waterford | Bethel | 325 | |
| Golf (Boys) | IV | East Catholic | Weston | 327 | |
| 2000 | Golf (Boys) | I | Simsbury | Glastonbury | 296 | |
| Golf (Boys) | II | Berlin | New Canaan | 320 | |
| Golf (Boys) | III | Waterford | Darien | 337 | |
| Golf (Boys) | IV | Northwest Catholic | Weston | 325 | |
| 1999 | Golf (Boys) | I | Cheshire | Simsbury | 309 | |
| Golf (Boys) | II | Pomperaug | Staples | 320 | |
| Golf (Boys) | III | Weston | Granby Memorial | 320 | |
| 1998 | Golf (Boys) | I | Simsbury | Fairfield Prep | 312 | |
| Golf (Boys) | II | Pomperaug | Darien | 312 | |
| Golf (Boys) | III | East Catholic | Valley Regional | 332 | |
| 1997 | Golf (Boys) | I | Ridgefield | | 303 | |
| Golf (Boys) | II | Staples | | 321 | |
| Golf (Boys) | III | Ellington | | 320 | |
| 1996 | Golf (Boys) | I | Amity | Glastonbury | 320 (won on 2nd hole of sudden death playoff) | |
| Golf (Boys) | II | Holy Cross | | 324 | |
| Golf (Boys) | III | Northwest Catholic | | 162 (9 holes) | |
| 1995 | Golf (Boys) | I | Fairfield Prep | | 311 | |
| Golf (Boys) | II | Holy Cross | | 311 | |
| Golf (Boys) | III | Stonington | | 319 | |
| 1994 | Golf (Boys) | I | Simsbury | Fairfield Prep | 317 | |
| Golf (Boys) | II | Watertown | Killingly | 339 (Won 3-hole playoff over Killingly) | |
| Golf (Boys) | III | St. Paul Catholic | Coventry | 320 | |
| 1993 | Golf (Boys) | I | Fairfield Prep | Fairfield | 320 | |
| Golf (Boys) | II | Berlin | Farmington & Tolland | 321 | |
| 1992 | Golf (Boys) | I | Fairfield | Staples | 312 (Won 3-hole playoff over Staples) | |
| Golf (Boys) | II | St. Paul Catholic | Watertown | 310 | |
| 1991 | Golf (Boys) | I | Fairfield | | 313 | |
| Golf (Boys) | II | Woodstock Academy | | 320 | |
| 1990 | Golf (Boys) | I | Fairfield Prep | Greenwich | 326 | |
| Golf (Boys) | II | Berlin | | 333 | |
| 1989 | Golf (Boys) | I | Staples | Fairfield | 330 | |
| Golf (Boys) | II | Berlin | Weston | 321 | |
| 1988 | Golf (Boys) | I | New Canaan | Staples | 323 | |
| Golf (Boys) | II | Berlin | RHAM | 307 | |
| 1987 | Golf (Boys) | I | Southington | | 309 | |
| Golf (Boys) | II | Berlin | | 332 | |
| 1986 | Golf (Boys) | I | Greenwich | | 317 | |
| Golf (Boys) | II | Portland | | 342 | |
| 1985 | Golf (Boys) | I | Fairfield Prep | | 311 | |
| Golf (Boys) | II | Avon | | 332 | |
| 1984 | Golf (Boys) | I | Wethersfield | | 315 | |
| Golf (Boys) | II | East Catholic | | 340 | |
| 1983 | Golf (Boys) | I | Fairfield Prep | | | |
| Golf (Boys) | II | Plainville | | | |
| 1982 | Golf (Boys) | I | Newington | | 312 | |
| Golf (Boys) | II | Suffield | Joel Barlow | 342 (Suffield won 3-hole playoff 55-57) | |
| 1981 | Golf (Boys) | I | Greenwich | | 314 | |
| Golf (Boys) | II | Waterford | | 318 | |
| 1980 | Golf (Boys) | I | Simsbury | | 315 | |
| Golf (Boys) | II | Waterford | | 325 | |
| 1979 | Golf (Boys) | I | Greenwich | | | |
| Golf (Boys) | II | Old Lyme/Stonington | | | |
| 1978 | Golf (Boys) | I | Amity Regional | | 315 | |
| Golf (Boys) | II | Joel Barlow | | 336 | |
| 1977 | Golf (Boys) | I | Hall | | 301 | |
| Golf (Boys) | II | Tolland | | 318 | |
| 1976 | Golf (Boys) | I | Staples | | 312 | |
| Golf (Boys) | II | East Catholic | | 301 | |
| 1975 | Golf (Boys) | I | Staples | | | |
| Golf (Boys) | II | East Catholic | | | |
| 1974 | Golf (Boys) | I | New Canaan | | | |
| Golf (Boys) | II | Old Saybrook | | | |
| 1973 | Golf (Boys) | I | Hall | | 313 | |
| Golf (Boys) | II | Old Saybrook | | 309 | |
| 1972 | Golf (Boys) | | Amity Regional | | 316 | |
| 1971 | Golf (Boys) | | Conard | | 305 | |
| 1970 | Golf (Boys) | | Simsbury | | 312 | |
| 1969 | Golf (Boys) | | Staples/Conard | (Co-Champions) | 304 | |
| 1968 | Golf (Boys) | | Staples | | 313 | |
| 1967 | Golf (Boys) | | Newington | | 318 | |
| 1966 | Golf (Boys) | | Hamden | | 316 | |
| 1965 | Golf (Boys) | | Southington | | 309 | |
| 1964 | Golf (Boys) | | Windsor | | 317 | |
| 1963 | Golf (Boys) | | Andrew Warde | | 334 | |
| 1962 | Golf (Boys) | L | Conard | | 315 | |
| Golf (Boys) | M | Amity Regional | | 311 | |
| 1961 | Golf (Boys) | | Amity Regional | | 318 | |
| 1960 | Golf (Boys) | | Stratford | | 313 | |
| 1959 | Golf (Boys) | | Manchester | | 327 | |
| 1958 | Golf (Boys) | | Manchester | | 326 | |
| 1957 | Golf (Boys) | | Stamford | | 326 | |
| 1956 | Golf (Boys) | | Stamford/Roger Ludlowe | | 337 | |
| 1955 | Golf (Boys) | | Wilbur Cross | | 327 | |
| 1954 | Golf (Boys) | | Manchester | | 329 | |
| 1953 | Golf (Boys) | | Greenwich | | 341 | |
| 1952 | Golf (Boys) | | Hall | | 335 | |
| 1951 | Golf (Boys) | | Stratford | | 339 | |
| 1950 | Golf (Boys) | | Danbury | | 334 | |
| 1949 | Golf (Boys) | | Manchester | | 327 | |
| 1948 | Golf (Boys) | | Bulkeley | | 331 | |
| 1947 | Golf (Boys) | | Bulkeley | | 325 | |
| 1946 | Golf (Boys) | | Danbury | | 363 | |
| 1941 | Golf (Boys) | | Newington | | 664 | |
| 1940 | Golf (Boys) | | Newington | | 641 | |
| 1939 | Golf (Boys) | | Newington | | 658 | |
| 1938 | Golf (Boys) | | Newington | | 603 | |
| 1937 | Golf (Boys) | | Fairfield | | 616 | |
| 1936 | Golf (Boys) | | Wethersfield | | 660 | |
| 1935 | Golf (Boys) | | Wethersfield | | 620 | |
| 1934 | Golf (Boys) | | Warren Harding | | 621 | |
| 1933 | Golf (Boys) | | Meriden | | 628 | |
| 1932 | Golf (Boys) | | Darien | | 648 | |
| 1931 | Golf (Boys) | | Darien | | 329 | |