| Year | Champion | Site | |
|---|---|---|---|
| 2024 | Michael Miller | Saint Andrew’s | |
| 2023 | James Nicholas | Whippoorwill | |
| 2022 | Bradford Tilley (a) | Sleepy Hollow | |
| 2021 | Rob M. Labritz | GlenArbor | |
| 2020 | Paul Pastore | Apawamis | |
| 2019 | Frank Bensel | Darien | |
| 2018 | Cameron Young (a) | Sunningdale | |
| 2017 | Daniel Balin | Wykagyl | |
| 2016 | Rob Labritz | GlenArbor | |
| 2015 | Daniel Balin | Brae Burn | |
| 2014 | David Pastore (a) | Metropolis | |
| 2013 | Colin McDade (a) | Manhattan Woods | |
| 2012 | Mike Ballo, Jr. | Wykagyl | |
| 2011 | Greg Bisconti | Brae Burn | |
| 2010 | Daniel Balin | Ardsley | |
| 2009 | Craig Thomas | Brooklawn | |
| 2008 | John Stoltz | Brae Burn | |
| 2007 | Tony DeMaria | GlenArbor | |
| 2006 | Ron Philo | Fairview | |
| 2005 | John Nieporte | Whippoorwill | |
| 2004 | Frank Bensel | Brae Burn | |
| 2003 | Dave Fusco | Tamarack | |
| 2002 | Tom Sutter | Brae Burn | |
| 2001 | Dave Fusco | Whippoorwill | |
| 2000 | Carl Alexander | Rockland | |
| 1999 | Bill Van Orman | Metropolis | |
| 1998 | Bruce Zabriski | Brae Burn | |
| 1997 | Bruce Zabriski | Ardsley | |
| 1996 | Ron McDougal | Tuxedo | |
| 1995 | Bruce Zabriski | Fenway | |
| 1994 | Delroy Cambridge | Knollwood | |
| 1993 | Rick Vershure | Brae Burn | |
| 1992 | Bobby Heins | Woodway | |
| 1991 | Rick Vershure | Siwanoy | |
| 1990 | Bobby Heins | Ardsley | |
| 1989 | Ron McDougal | Tuxedo | |
| 1988 | Bobby Heins | Stanwich | |
| 1987 | Mike White | Brae Burn | |
| 1986 | Bill Britton | Greenwich | |
| 1985 | Evan Schiller | Westchester | |
| 1984 | Bruce Douglass | Wykagyl | |
| 1983 | Bobby Heins | Stanwich | |
| 1982 | Bobby Heins | Sunningdale | |
| 1981 | Bobby Heins | Shorehaven | |
| 1980 | Gene Borek | Wykagyl | |
| 1979 | John Gentile | Sleepy Hollow | |
| 1978 | John Gentile | Knollwood | |
| 1977 | Tom Joyce | Brooklawn | |
| 1976 | John Ruby | Tamarack | |
| 1975 | John Gentile | Stanwich | |
| 1974 | Kelley Moser | Fairview | |
| 1973 | John Gentile | Sunningdale | |
| 1972 | Don Massengale | Briar Hall | |
| 1971 | David Ragaini (a) | Wykagyl | |
| 1970 | Juhn Buczek | Brae Burn | |
| 1969 | Mike Krak | Ardsley | |
| 1968 | Denny Lyons (a) | Stanwich | |
| 1967 | Roy Pace | Knollwood | |
| 1966 | Frank Wharton | Briar Hall | |
| 1965 | Terry Wilcox | Fairview | |
| 1964 | Terry Wilcox | Sleepy Hollow | |
| 1963 | Doug Ford | Vernon Hills | |
| 1962 | Gil Cavanaugh/Roger Ginsberg (a) | Bonnie Briar | |
| 1961 | Doug Ford | Apawamis | |
| 1960 | Claude Harmon | Wee Burn | |
| 1959 | Robert Watson | Metropolis | |
| 1958 | Fred Annon | Knollwood | |
| 1957 | Mickey Homa | Leewood | |
| 1956 | Mickey Homa | Winged Foot | |
| 1955 | Mickey Homa | Wee Burn | |
| 1954 | Harman Barron | Bonnie Briar | |
| 1953 | Claude Harmon | Knollwood | |
| 1952 | Fred Annon | Willows | |
| 1951 | Claude Harmon | Sleepy Hollow | |
| 1950 | Claude Harmon | Bonnie Briar | |
| 1949 | Jack Patroni | Apawamis | |
| 1948 | Tony Manero | Knollwood | |
| 1947 | Claude Harmon | Gedney Farms | |
| 1946 | Claude Harmon | Bonnie Briar | |
| 1943-’45 No Competitions – World War II | |||
| 1942 | Paul Runyan | Metropolis | |
| 1941 | Mike Turnesa | Apawamis | |
| 1940 | Ben Hogan | Mount Vernon | |
| 1939 | Paul Runyan | Lawrence Farms | |
| 1938 | Frank Moore | Sunningdale | |
| 1937 | Frank Moore | Green Meadow | |
| 1936 | Paul Runyan | Metropolis | |
| 1935 | Paul Runyan | Fenimore | |
| 1934 | Paul Runyan | Rockwood Hall | |
| 1933 | Mike Turnesa | Bonnie Briar | |
| 1932 | Tony Manero | Wykagyl | |
| 1931 | Paul Runyan | Green Meadow | |
| 1930 | Willie McFarlane | Fenimore | |
| 1929 | Bobby Cruickshank | Gedney Farms | |
| 1928 | Bill Melhorn | Oak Ridge | |
| 1927 | Bobby Cruickshank | Fenimore | |
| 1926 | Johnny Farrell | Century | |
| 1925 | Mike J. Brady | Briarcliff Lodge | |
| 1924 | Willie McFarlane | Winged Foot | |
| 1923 | George McLean | Mount Kisco | |
| 1922 | Willie McFarlane | Quaker Ridge | |
| 1921 | Jack Dowling | Pelham | |
| 1920 | Tom Kerrigan | Westchester Hills | |
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