1986
| Norman McHugh
| Staples
| Distance
|
1987
| Mike Remigino
| Northwest Catholic
| Distance
|
1988
| Harvey Kendall
| Hartford Public
| Triple jump
|
1989
| JT Burke
| Xavier
| Distance
|
1990
| Harvey Kendall
| Hartford Pubic
| Triple jump
|
1991
| Travis Brunson
| Notre Dame - West Haven
| Sprints
|
1992
| Gardner Lewis
| Hamden
| Jumps
|
1993
| Jerome Young
| Prince Tech
| Sprints
|
1994
| Aaron Haynes
| Wilbur Cross
| Hurdles
|
1995
| Jerome Young
| Prince Tech
| Sprints
|
1996
| Steve McHugh
| Xavier
| Distance
|
1997
| Dan Wilson
| Notre Dame - West Haven
| Distance
|
1998
| Hunter Spencer
| EO Smith
| Distance
|
1999
| Shelldon Simpson
| East Hartford
| Sprints
|
2000
| Jermelle Lewis
| Bloomfield
| Sprints and relays
|
2001
| Glenn McFadden
| Hillhouse
| Sprints and long jump
|
2002
| Andre Laboy
| Danbury
| Distance
|
2003
| Ahmed Haji
| Conard
| Distance
|
2004
| Gavin Coombs
| Griswold
| Distance
|
2005
| Myles Bradley
| Norwich Free Academy
| Long jump, triple jump, hurdles
|
2006
| James Nixon
| Hyde Leadership
| Sprints
|
2007
| Terrell Wilks
| Hillhouse
| Sprints
|
2008
| Donn Cabral
| Glastonbury
| Distance
|
2009
| Cas Loxsom
| Wilbur Cross
| Middle distance
|
2010
| Chris Fitzsimons
| Hamden
| Middle distance
|
2011
| John Wlasuk
| Newtown
| Throws
|
2012
| Jake Scinta
| Cheshire
| Jumps
|
2013
| Henry Wynne
| Staples
| Middle distance and long distance
|
2014
| Tyler Latham
| Fitch
| Hurdles and javelin
|
2015
| Spencer Brown
| Wilton
| Middle distance and long distance
|
2016
| Eric Van der Els
| Brien McMahon
| Distance
|
2017
| Tyler Glenn
| Trumbull
| Middle distance
|
2018
| Justin Forde
| Brien McMahon
| Jumps
|
2019
| Justin Forde
| Brien McMahon
| Jumps
|
2020
| Sean Dixon-Bodie
| Bloomfield
| Jumps
|
2021
| Gavin Sherry
| Conard
| Distance
|
2022
| Gary Moore, Jr
| Hillhouse
| Throws
|