| Tournament | Winners | Runners Up | Scores |
| 2019 Men's 50+ Senior | Jon Lubow
Jerry Albrikes | Mike Gillespie
Ron Erskine | NA |
| 2018 Men’s 50+ Senior | Ron Erskine
Michael Gillespie | Scott Bondurant
Jon Lubow | 6-3, 6-1 |
| 2017 Men's 50+ Senior | Michael Gillespie
Ron Erskine | Jim Kaufman
Russ Jellinek | 6-2, 7-5 |
| 2016 Men's 50+ Senior | Ron Erskine
Michael Gillespie | Mike Atkinson
John Milbank | 6-3, 6-1 |
| 2015 Men's 50+ Senior | Ron Erskine
Michael Gillespie | Jim Kaufman
Rusty Wright | 6-2, 6-3 |
| 2014 Men's 50+ Senior | Ron Erskine
Michael Gillespie | Ed Gartner
John Shehadi | 6-3, 6-2 |
| 2013 Men's 50+ Senior | Ron Erskine
Michael Gillespie | Ed Gartner
John Shehadi | 3-6, 6-1, 7-5 |
| 2012 Men's 50+ Senior | Ron Erskine
Michael Gillespie | Scott Bondurant
Tim McAvoy | 6-4, 3-6, 6-3 |
| 2011 Men's 50+ Senior | Scott Bondurant
Bill Fiedler | Fritz Odenbach
Rusty Wright | 7-6, 6-1 |
| 2010 Men's 50+ Senior | Scott Bondurant
Tim McAvoy | Chip Morrow
Peter Redpath | 6-1, 6-4 |
| 2009 Men's 50+ Senior | Scott Bondurant
Tim McAvoy | Chip Morrow
Peter Redpath | 7-5, 6-2 |
| 2008 Men's 50+ Senior | Jim Kaufman
Bob Kleinert | Tim McAvoy
John Stefanik | 6-4, 6-2 |
| 2007 Men's 50+ Senior | Peter Redpath
John Stefanik | Stephen W. Baird
Bob Kleinert | 6-1, 6-3 |
| 2006 Men's 50+ Senior | Peter Redpath
John Stefanik | Ivan Harlow
Mike Palmer | 6-2, 6-2 |
| 2005 Men's 50+ Senior | Jean Kempner
Jim McNitt | Jeff Hodges
Hank Irvine | N/A |
| 2004 Men's 50+ Senior | John Embree
John Stefanik | Scott Estes
Jean Kempner | 7-5, 6-3 |
| 2003 Men's 50+ Senior | Jean Kempner
Jim McNitt | Steve Nycum
John Stefanik | 3-6, 7-5, 6-3 |
| 2002 Men's 50+ Senior | Jeff Hodges
Hank Irvine | Stephen W. Baird
Burke Hayes | 6-4, 6-1 |
| 2001 Men's 50+ Senior | John Adams
Stephen W. Baird | Scott Estes
Steve Nycum | 6-4, 5-7, 6-2 |
| 2000 Men's 50+ Senior | John Adams
Stephen W. Baird | Jeff Hodges
Jack Hogan | 6-3, 7-6 (7-1) |
| 1999 Men's 50+ Senior | Scott Estes
Dan Galves | Tom Caputo
Gary Cochrane | 3-6, 6-1, 7-6 |
| 1998 Men's 50+ Senior | Richard Hornidge
Bruce Mahler | Scott Estes
Dan Galves | 6-4, 4-6, 6-4 |
| 1997 Men's 50+ Senior | Dave Connell
Jack Hogan | Alan M Graham
Stu Opdycke | 6-1, 4-6, 6-4 |
| 1996 Men's 50+ Senior | Scott Estes
Dan Galves | Dave Connell
Jack Hogan | 7-5, 3-6, 7-6 |
| 1995 Men's 50+ Senior | Mike Burton
Duke Felt | Richard Hornidge
Craig Mielke | 6-3, 6-4 |
| 1994 Men's 50+ Senior | Duke Felt
Craig Mielke | Roy Anderson
Alan Brasher | 6-2, 6-4 |
| 1993 Men's 50+ Senior | Duke Felt
Craig Mielke | Roy Anderson
Alan Brasher | 7-6, 7-5 |
| 1992 Men's 50+ Senior | Duke Felt
Craig Mielke | Dick Haverland
David Dickenson | 6-3, 6-4 |
| 1991 Men's 50+ Senior | David Dickenson
Dick Haverland | Keith Butterfield
Charles Parton | 6-3, 6-3 |
| 1990 Men's 50+ Senior | David L Childs
William P Childs | Tom Beach
Ted Prince | 7-6, 6-4 |
| 1989 Men's 50+ Senior | David Dickenson
Duke Felt | Roy Anderson
Joe Holmes | N/A |
| 1988 Men's 50+ Senior | Peter Chase
Gordon S Gray | Rich Lombard
Larry Waterhouse | N/A |
| 1987 Men's 50+ Senior | David L Childs
William P Childs | Howard A Sipe
Jack L Watson | N/A |
| 1986 Men's 50+ Senior | David L Childs
William P Childs | Howard A Sipe
Jack L Watson | 5-7, 6-3, 6-2 |
| 1985 Men's 50+ Senior | Howard A Sipe
Jack L Watson | Chet Kermode
Bill Schneebeck | 6-3, 7-6 (7-3) |
| 1984 Men's 50+ Senior | Ken Hipkins
Arch Van Vlaanderen | Charles F. Baird
Roger Lankenau | 7-6, 7-5 |
| 1983 Men's 50+ Senior | Chet Kermode
Bill Schneebeck | Sel Atherton
Jim Garivaltis | 2-6, 7-5, 6-3 |
| 1982 Men's 50+ Senior | Charles F. Baird
George Schmid | St John Bain
Bill Schneebeck | 6-3, 4-6, 6-2 |
| 1981 Men's 50+ Senior | Sel Atherton
Jim Garivaltis | Dave Kelton
Ted Peterson | 6-1, 6-7, 6-2 |
| 1980 Men's 50+ Senior | St John Bain
Bill Schneebeck | Robert A Brown
George Reynolds | 6-2, 6-4 |
| 1979 Men's 50+ Senior | St John Bain
Bill Schneebeck | Robert A Brown
George Reynolds | 7-6, 7-6 |
| 1978 Men's 50+ Senior | Robert A Brown
George Reynolds | Charles F. Baird
Roger Lankenau | 6-3, 4-6, 7-5 |
| 1977 Men's 50+ Senior | Charles F. Baird
Roger Lankenau | St John Bain
Eric Yeister | 6-4, 6-3 |
| 1976 Men's 50+ Senior | Charles F. Baird
Roger Lankenau | A E Muth
George Schmid | 6-3, 6-1 |
| 1975 Men's 50+ Senior | Charles F. Baird
Edmund R Swanberg | A E Muth
George Schmid | 6-1, 6-4 |
| 1974 Men's 50+ Senior | Charles F. Baird
Edmund R Swanberg | George R Harrison
Richard K Hebard | 6-4, 3-6, 6-3 |
| 1973 Men's 50+ Senior | Charles F. Baird
Edmund R Swanberg | Lyman Andrus
J L Dugan | 6-2, 6-2 |
| 1972 Men's 50+ Senior | Charles F. Baird
Edmund R Swanberg | Robert Baldwin
George Schmid | 6-3, 7-5 |
| 1971 Men's 50+ Senior | Robert Baldwin
George Schmid | Tad Bowen
Sidney Sweet Jr | 6-4, 6-1 |
| 1970 Men's 50+ Senior | A.H. (Zan) Carver, Jr.
Richard K Hebard | Tad Bowen
Sidney Sweet Jr | 6-3, 8-6 |
| 1969 Men's 50+ Senior | Tad Bowen
Sidney Sweet Jr | Charles Dedrick
Peter Shonk | 6-4, 6-4 |
| 1968 Men's 50+ Senior | George Lowman
William E Pardoe | A.H. (Zan) Carver, Jr.
George R Harrison | 4-6, 7-5, 6-1 |
| 1967 Men's 50+ Senior | George Lowman
William E Pardoe | Richard K Hebard
Donald Wheaton | 6-2, 6-0 |
| 1966 Men's 50+ Senior | George Lowman
William E Pardoe | William Park
Mansfield Sprague | 6-2, 6-1 |
| 1965 Men's 50+ Senior | Richard K Hebard
Sidney Sweet Jr | Harrison Cole
Kenneth LaVine | 6-1, 6-1 |
| 1964 Men's 50+ Senior | Germain Glidden
William Park | Charles Buchler
Berkeley D Johnson | 7-5, 8-6 |
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