| 1948 | Marcy Sperry | Jack Whitner | 1949 | Alfred Whitney | Bob Whitney |
| 1950 | Phil Guiles | Alfred Whitney | 1951 | Alfred Whitney | Howard Whitney |
| 1952 | Alfred Whitney | Bob Whitney | 1953 | Alfred Whitney | Bill Densmore |
| 1954 | Dick Goodnow | Blair Whitham | 1955 | Mike Kraft | Dennis Moore |
| 1956 | Jay Goodnow | Bob Whitney | 1957 | Joe O’Connor | Blair Whitham |
| 1958 | Alfred Whitney | George McElroy Jr. | 1959 | Jim Perry | Bob Whitney |
| 1960 | Alfred Whitney | Joe O’Connor | 1961 | Tom Bushman | Howard Whitney |
| 1962 | Ivory Littlefield Jr. | Philip Howe | 1963 | Dennis Moore | David Milton |
| 1964 | Dennis Moore | Albert Kreik | 1965 | Marchall Greene | Richard Abbott |
| 1966 | Everett Webster | John Shaughnessy | 1967 | Thomas Allen Jr. | George Parker II |
| 1968 | Chris Bice | David Nichols | 1969 | Jim Perry | D. J. Hart |
| 1970 | Robert Whitney | Alan Howe | 1971 | Jud Goodnow III | David Hall |
| 1972 | Jud Goodnow III | Fred Trafton | 1973 | Richard Abbott | Phil Carter |
| 1974 | Herb Maynard | Nick Littlefield | 1975 | Stephen Tiarks | Thomas Waters |
| 1976 | William Morgan | Geoffrey Parker | 1977 | Dennis Pomerleau | Jim Perry |
| 1978 | Terry Hart | Herb Maynard | 1979 | Carl Johnson | David Milton |
| 1980 | Jud Goodnow III | David Smith | 1981 | Rusty Sampson | David Milton Sr. |
| 1982 | Carl Johnson | Frank Shaughnessy | 1983 | Rusty Sampson | Terry Hart |
| 1984 | David Nichols | Stephen Tiarks | 1985 | Rusty Sampson | Wallace Whitney |
| 1986 | Terry Hart | David Milton Jr. | 1987 | Wallace Whitney | Frank Lowenstein |
| 1988 | Terry Hart | James Perry | 1989 | Larry Sigler | Bill Davis |
| 1990 | Rusty Sampson | Rich Bisk | 1991 | Jack Novia | Bud Brooks |
“Tennis may well be called a royal game, have been popular with various Kings of England and France. In the ball games of the Greeks and Romans, we see the rudiments of the French Je de paume, which is in all probability the ancestor of modern tennis in a direct line.”
| 1992 | Rusty Sampson | Carl Johnson | 1993 | Terry Hart | Rich Bisk |
| 1994 | Steve Recupero | Bob Paradice | 1995 | Steve Recupero | John Stimpson |
| 1996 | John Stimpson | Larry Sigler | 1997 | Rich Bisk | Dan Spedding |
| 1998 | Steve Recupero | Bart Rubin | 1999 | Rusty Sampson | Bud Brooks |
| 2000 | Tim Goodnow | Steve Recupero | 2001 | Terry Hart | Eric Booth |
| 2002 | Rusty Sampson | Billy Shaughnessy | 2003 | Peter Crowley | Steve Recupero |
| 2004 | Rich Bisk | Wayne Lilley | 2005 | David Cronin | Brian Hobbs |
| 2006 | Paul Durand | Dan Spedding | 2007 | David Cronin | Frank Shaughnessy |
| 2008 | John Getchell | Rusty Sampson | 2009 | Alex Samoiloff | Larry Sigler |
| 2010 | David Lowenthal | Nick Wiles | 2011 | Kelton Burbank | John Carlson |
| 2012 | David Cronin | Tom Lawton | 2013 | Jeff Eska | Jason Tomforde |
| 2014 | Tom Lawton | Roberto Mahoney | 2015 | ||
| 2016 | 2017 | ||||
| 2018 | 2019 | ||||
| 2020 | 2021 |