| Year | Champion | Site |
|---|---|---|
| 2023 | Cormack Meldrum | Redding |
| 2022 | Jonathan Oakes | Silvermine |
| 2021 | Tyler Donnellan | Westchester Hills |
| 2020 | Douglas Beney | Silvermine |
| 2019 | Douglas Beney | Wilywyck |
| 2018 | Charlie Berridge | Fairview |
| 2017 | Matt Minerva, Jr. | Knollwood |
| 2016 | Brent Ito | Knollwood |
| 2015 | Addison Cilmi | Knollwood |
| 2014 | Kevin Allyn | Knollwood |
| 2013 | Solomon Thompson | Knollwood |
| 2012 | Christian Cavaliere | Knollwood |
| 2011 | Sean Trainor | Knollwood |
| 2010 | Theo Humphrey | Knollwood |
| 2009 | Michael Miller | Knollwood |
| 2008 | Peter Ballo | Knollwood |
| 2007 | Michael Miller | Knollwood |
| 2006 | Michael Ballo | Knollwood |
| 2005 | Joe Foley | Knollwood |
| 2004 | Chris Scialo | Knollwood |
| 2003 | Chris Turnesa | Knollwood |
| 2002 | John Jamgochian | Knollwood |
| 2001 | Mike Larkin | Knollwood |
| 2000 | Michael Adams | Knollwood |
| 1999 | Chris Damiano | Knollwood |
| 1998 | Tim Conners | Knollwood |
| 1997 | Jeff Marcinowski | Knollwood |
| 1996 | Johnson Wagner | Knollwood |
| 1995 | Johnson Wagner | Knollwood |
| 1994 | Taylor Walsh | Knollwood |
| 1993 | Sean McGugian | Knollwood |
| 1992 | Brad Kittsley | Knollwood |
| 1991 | Brad Kittsley | West Point |
| 1990 | Brad Kittsley | Osiris |
| 1989 | Scott Miller | Powelton |
| 1988 | Charlie Rodgers | West Point |
| 1987 | John Lick | Bedford |
| 1986 | Louis Stein | Scarsdale |
| 1985 | Niels Murphy | Willow Ridge |
| 1984 | Robert Byrnes | Ardsley |
| 1983 | Jerry Springer | Whippoorwill |
| 1982 | John Miller | Mahopac |
| 1981 | Donald Edwards | Bonnie Briar |
| 1980 | William Bisceglia | Bedford |
| 1979 | Bradley Steinthal | Mahopac |
| 1978 | Edward Tompkins | Innis Arden |
| 1977 | Jon Doppelt | Ardsley |
| 1976 | Guy Kennen | Bedford |
| 1975 | Bob Cloughen, Jr. | Pelham |
| 1974 | Emmett Fitzgerald | Mahopac |
| 1973 | Timothy Olsen | Westchester Hills |
| 1972 | Martin Nolletti, Jr. | Whippoorwill |
| 1971 | Chip Roe | Mahopac |
| 1970 | Feroie Catropa | Hudson Hills |
| 1969 | Gary Stauderman | - |
| 1968 | Timothy Rockett | Ardsley |
| 1967 | William Harmon | Westchester Hills |
| 1966 | William Killea | Ardsley |
| 1965 | Rod Ferguson | Bonnie Briar |
| 1964 | Harry Hillman | Apawamis |
| 1963 | Mike Turnesa, Jr. | Leewood |
| 1962 | Dan Mazzilli | Pelham |
| 1961 | Joseph Vallo, Jr. | Ardsley |
| 1960 | Donald Bank | West Hills |
| 1959 | David Mance | - |
| 1958 | Peter Bisconti, Jr. | Sleepy Hollow |
| 1957 | Clement Miner, Jr. | Ardsely |
| 1956 | Clement Miner, Jr. | Westchester Hills |
| 1955 | Frank Malara, Jr. | Ardsley |
| 1954 | Peter Nisselson | Wykagyl |
| 1953 | Peter Nisselson | Bonnie Briar |
| 1952 | Arnold Lipman | Hampshire |
| 1951 | Arnold Lipman | Winged Foot |
| 1950 | Paul Kelly | Knollwood |
| 1949 | Paul Kelly | Westchester Hills |
| 1948 | William Rickenbacker | Apawamis |
| 1947 | William Rickenbacker | Westchester Hills |
| 1946 | Paul Kelly | Briar Hills |
| 1942-'45 No Competitions | ||
| 1941 | Douglas Ford | - |
