| Year | Champion | Site |
|---|---|---|
| 2026 | Tommy Mangan | Ardsley |
| 2025 | Mike Rothberg | Trump – Hudson Valley |
| 2024 | Jackson Fretty | Tamarack |
| 2023 | Ryan Coughlin | GlenArbor |
| 2022 | Ryan Coughlin | Metropolis |
| 2021 | Chris Scialo | Paramount CC |
| 2020 | Brad Tilley | Knollwood |
| 2019 | Christian Cavaliere | Winged Foot |
| 2018 | Christian Cavaliere | Brooklawn |
| 2017 | Christian Cavaliere | Whippoorwill |
| 2016 | Josh Goldenberg | Ardsley |
| 2015 | Luke Feehan | Rockrimmon |
| 2014 | Jonathan Renza | Westchester CC |
| 2013 | Colin McDade | Brae Burn |
| 2012 | Michael Miller | Rockrimmon |
| 2011 | Cameron Young | Trump National – Hudson Valley |
| 2010 | Jonathan Renza | Woodway |
| 2009 | Michael Ballo, Jr. | Fairview |
| 2008 | Max Buckley | Rockrimmon |
| 2007 | Michael Quagliano | Stanwich |
| 2006 | Joel Lulla | Sleepy Hollow |
| 2005 | Brad Tilley | Sunningdale |
| 2004 | Michael Reardon | Metropolis |
| 2003 | Charles Del Priore, Jr. | Woodway |
| 2002 | Andrew Svoboda | Fenway |
| 2001 | Chris Damiano | Knollwood |
| 2000 | Joe Sommers | Tamarack |
| 1999 | Greg Rohlf | Old Oaks |
| 1998 | Greg Rohlf | Fenway |
| 1997 | Greg Rohlf | Sleepy Hollow |
| 1996 | Jack Curran | Sunningdale |
| 1995 | Bill Hackett | Siwanoy |
| 1994 | Greg Bisconti | Old Oaks |
| 1993 | Brad Kittsley | Tuxedo |
| 1992 | George Zahringer III | Stanwich |
| 1991 | Tom Yellin | Metropolis |
| 1990 | Tom Hamilton | Century |
| 1989 | Jim Turnesa | Wee Burn |
| 1988 | Jim Turnesa | Bonnie Briar |
| 1987 | Jerry Springer | Ardsley |
| 1986 | Jon Doppelt | Woodway |
| 1985 | Jon Saxton | Tuxedo |
| 1984 | Jon Saxton | Tamarack |
| 1983 | Jon Saxton | Brae Burn |
| 1982 | Jon Saxton | Metropolis |
| 1981 | Jon Saxton | Salem |
| 1980 | Bruce Aubin | Brae Burn |
| 1979 | George Zahringer III | Sunningdale |
| 1978 | Jon Doppelt | Siwanoy |
| 1977 | David Muraskin | Woodway |
| 1976 | David Muraskin | Fenway |
| 1975 | John Dalrymple | Winged Foot |
| 1974 | Gregory Zorila | Ridgeway |
| 1973 | Gregory Zorila | Metropolis |
| 1972 | Mike Turnesa, Jr. | Fairview |
| 1971 | Dr. Jerry Sacks | Tamarack |
| 1970 | John Gentile, Jr. | Sunningdale |
| 1969 | Gregory Zorila | – |
| 1968 | George S. Dillon, Jr. | Sleepy Hollow |
| 1967 | Ron T. Mahood | – |
| 1966 | Craig Wood Harmon | West Hills |
| 1965 | Craig Wood Harmon | Apawamis |
| 1964 | Clem Miner, Jr. | Knollwood |
| 1963 | Jerry Courville, Sr. | Metropolis |
| 1962 | Roger Ginsberg | Wykagyl |
| 1961 | Frank Malara, Jr. | Fairview |
| 1960 | James E. Iverson | Bonnie Briar |
| 1959 | Paul E. Kelly | Siwanoy |
| 1958 | Joseph Kryla, Jr. | Pelham |
| 1957 | Peter Nisselson | Sleepy Hollow |
| 1956 | Joseph Marra | Whipporwill |
| 1955 | J. Henry Attas | Apawamis |
| 1954 | Lloyd D. Ribner | Metropolis |
| 1953 | Paul Kelly | Sleepy Hollow |
| 1952 | Robert Kuntz | Bonnie Briar |
| 1951 | J. Henry Attas | Pelham |
| 1950 | Thomas J. Goodwin | Winged Foot |
| 1949 | Lloyd D. Ribner | Knollwood |
| 1948 | Joseph Gagliardi | Bonnie Briar |
| 1947 | Douglas Ford | Wee Burn |
| 1946 | Thomas J. Goodwin | Metropolis |
| 1942-’45 No Competition | ||
| 1941 | Jack Creavy | Old Oaks |
| 1940 | Thomas J. Goodwin | – |
| 1939 | Jack Creavy | – |
| 1938 | William P. Turnesa | – |
| 1937 | William P. Turnesa | Century |
| 1936 | William P. Turnesa | – |
| 1935 | Thomas J. Goodwin | Sunningdale |
| 1934 | Richard D. Chapman | Bonnie Briar |
| 1933 | William P. Turnesa | Winged Foot |
| 1932 | Leonard Martin | Westchester CC |
| 1931 | Palmer Kountze | Mount Kisco |
| 1930 | P Miller Jones | Siwanoy |
| 1929 | George T. Brush | Green Meadow |
| 1928 | George T. Brush | Westchester CC |
| 1927 | R. W. Woolworth | Briar Hills |
| 1926 | John G. Anderson | Westchester CC |
| 1925 | John G. Anderson | Wykagyl |
| 1924 | George I. Lawyer | Quaker Ridge |
| 1923 | E. E. Sturgis | Sleepy Hollow |
| 1922 | E. E. Sturgis | Hudson River |
| 1921 | J. S. Worthington | Ardsley |
| 1920 | J. S. Worthington | Dunwoodie |
| 1919 | Leslie Conely | Apawamis |
| 1918 | John G. Anderson | Siwanoy |
| 1917 | John G. Anderson | Scarsdale |
| 1916 | Reginald Lewis | Wykagyl |
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