| Year | Champion | Site | |
|---|---|---|---|
| 2022 | Patrick Mainey & Sean McNally | Wiltwyck | |
| 2021 | Patrick Mainey & Sean McNally | Powelton | |
| 2020 | Event not held | ||
| 2019 | Bear Carlson & Tore Carlson | Powelton | |
| 2018 | Bear Carlson & Nils Carlson | Anglebrook | |
| 2017 | Rob Johnson & John Vignola | Anglebrook | |
| 2016 | Paul Pastore & Jeff Santilli | St. Andrew’s | |
| 2015 | Matt Minerva & Chris Strnad | St. Andrew’s | |
| 2014 | Stu Kaufman & Earl Rix | St. Andrew’s | |
| 2013 | Matt Minerva & Chris Strnad | St. Andrew’s | |
| 2012 | Chris Kelly & Danny Blumber | St. Andrew’s | |
| 2011 | Matt Minerva & Chris Strnad | St. Andrew’s | |
| 2010 | Conor & Colin McDade | St. Andrew’s | |
| 2009 | Robert Johnson & Steve Krasner | St. Andrew’s | |
| 2008 | Jon Gruenber & Toby Stern
Andrew Shorthall & Tyler Gilmour |
St. Andrew’s | |
| 2007 | Jeff Day & Richard Feldman | St. Andrew’s | |
| 2006 | D.J. Cimillo & Robert Johnson | St. Andrew’s | |
| 2005 | Phil Stone & Tim Hegarty | St. Andrew’s | |
| 2004 | Russ Giglio & Tim Hand | St. Andrew’s | |
| 2003 | Jim Dufficy & Jeff Teasdale | St. Andrew’s | |
| 2002 | Michael Doetsch & Joe Collins | St. Andrew’s | |
| 2001 | Jim Graham & Andrew Svoboda | St. Andrew’s | |
| 2000 | Owen O’Neil & Frank Queally | St. Andrew’s | |
| 1999 | Judy Carlson & Warren Vanderbush | St. Andrew’s | |
| 1998 | Todd Payne & Ray Bufkin | St. Andrew’s | |
| 1997 | Jack Lewin & Tony Rolfe | Whippoorwill | |
| 1996 | Pat Mahoney & Mike Caggiano | Waccabuc | |
| 1995 | Steve Nosonowitz & Jim Bernard | Mount Kisco | |
| 1994 | Paul Wise & Joel Lulla | Ardsley | |
| 1993 | Eddie Bass & Charles Theiss | Whippoorwill | |
| 1992 | Howard & Glenn Hertzberg | Fairview | |
| 1991 | Tom & Tom Jr. Zeuthen | Bonnie Briar | |
| 1990 | Joe Sommers & Kevin McEvoy | Brooklawn | |
| 1989 | Harry Jr. & Harry III Gerdelstone | Brae Burn | |
| 1988 | Todd Richter & Ben Kirschenbaum | Wykagyl | |
| 1987 | John Pretak & Harry Gerdelstone | Fenway | |
| 1986 | Jay Jennison & Pete Williams | Burning Tree | |
| 1985 | Steve Murphy & Keith Rick | Old Oaks | |
| 1984 | Jon Saxon & Tom Hamilton | Fairview | |
| 1983 | Jon Saxon & Bill Shea | Woodway | |
| 1982 | Alan Helfer & Andres Siderowf | Brooklawn | |
| 1981 | Bruce Aubin & Dave Smith, Jr. | Sleepy Hollow | |
| 1980 | Richard Bodine & John Revenaugh | Tamarack | |
| 1979 | Al Butera & Todd Payne | Ridgewood | |
| 1978 | Jeff Weiss & Richard Rubin | Wee Burn | |
| 1977 | Ed Travis & Bruce Simmons | Stanwich | |
| 1976 | J. M. Peelor & John Pretak | Old Oaks | |
| 1975 | Edward & John Schneider | Knollwood | |
| 1974 | Bob Stauderman & Bob Keener | Brae Burn | |
| 1973 | Bob Botsford & Ralph DeStefano | Dutchess | |
| 1972 | Frank Gonda & Joe Kryla, Jr. | Sunningdale | |
| 1971 | Charles McAdams, Jr. & Michael Hanson | Century | |
| 1970 | James Maver, Jr. & Walter Ullrich | Round Hill | |
| 1969 | Peter Bisconti & Franklin Simon | – | |
| 1968 | James Maver, Jr. & Richard Harmon | Wykagyl | |
| 1967 | A. L. Dreyfus & Pat Fiori | – | |
| 1966 | Ford White & James Maver | Siwanoy | |
| 1965 | Ford White & Richard Doetsch | Century | |
| 1964 | Joe, Sr. & Joe, Jr. Kryla | Wykagyl | |
| 1963 | James Fisher & Claude Harman, Jr. | Whippoorwill | |
| 1962 | Don Scanlon & Pete Williams | Darien | |
| 1961 | Tommy Goodwin & Pete Williams | Century | |
| 1960 | James Iverson & Joe Pittore | Fairview | |
| 1959 | Paul Kelly & Dave Mance | – | |
| 1958 | Willie Turnesa & Fred Fiori | St. Andrew’s | |
| 1957 | Willie Turnesa & Fred Fiori | Metropolis | |
| 1956 | Michael Volpe & Anthony Sforza | Sleepy Hollow | |
| 1955 | Joe Gonda, Jr. & Frank Malara, Jr. | Briar Hall | |
| 1954 | J. Atlas & Lloyd Ribner | Harrison | |
| 1953 | J. Atlas & Lloyd Ribner | Sunningdale | |
| 1952 | J. Risoli & M. Volpe | Century | |
| 1951 | Jerry Cole & Lloyd Ribner | Metropolis | |
| 1950 | J. Atlas & J. Galgano* | Whippoorwill | |
| 1949 | Lloyd Ribner | Sleepy Hollow | |
| 1948 | Doug Ford | Metropolis | |
| 1947 | Ray Billows | Knollwood | |
| 1946 | Tommy Goodwin | Hudson River | |
| 1942-’45 No Competitions – World War II | |||
| 1941 | Ray Billows | Sleepy Hollow | |
| 1940 | Tommy Goodwin | – | |
| 1939 | John Burke | – | |
| 1938 | Ray Billows | – | |
| 1937 | Ray Billows | Winged Foot | |
| 1936 | Ray Billows | – | |
| 1935 | Tommy Goodwin | Westchester CC | |
| 1934 | Richard Chapman | Green Meadow | |
| 1933 | Robert Lester | Sunningdale | |
| 1932 | John E. Parker, Jr. | Hudson River | |
| 1931 | George Voight | Ardsley | |
| 1930 | Jess Sweetser | Green Meadow | |
| 1929 | Jess Sweetser | Wykagyl | |
| 1928 | Jess Sweetser | Wykagyl | |
| 1927 | J. Wood Platt | Siwanoy | |
| 1924-’26 No Competitions | |||
| 1923 | Jess Sweetser | – | |
| 1922 | Leslie Conley | – | |
| 1921 | Jess Sweetser | – | |
| 1920 | Jess Sweetser | – | |
| 1919 | Ned Sawyer | – | |
*the competition changed to a Best Ball of Two in 1950
