| 2024 | John Stevenson | Sunnybrook GC | Noah Wallace | Chesapeake Bay GC | 2&1 | The Ridge at Back Brook |
| 2023 | John Stevenson | LuLu CC | Winston Kelenc-Blank | Saucon Valley CC | 4&3 | LuLu CC |
| 2022 | Joshua Ryan | The 1912 Club | Nathan Guertler | Merion GC | 5&4 | Bala GC |
| 2021 | Joshua Ryan | The 1912 Club | Morgan Lofland | Phoenixville CC | 4&3 | Overbrook GC |
| 2020 | Joshua Ryan | GAP Youth on Course | Corey Haydu | Spring Mill CC | 6&4 | The 1912 Club |
| 2019 | Austin Barbin | Loch Nairn GC | Patrick Sheehan | Talamore CC | 5&4 | Coatesville CC |
| 2018 | Ryan Tall | Spring Ford CC | William Mirams | Shawnee CC | 4&3 | Blue Bell CC |
| 2017 | Dawson Anders | Indian Valley CC | Brian Isztwan | Huntingdon Valley CC | 6&4 | Spring Ford CC |
| 2016 | David Colleran, Jr. | Overbrook GC | Marty McGuckin | RiverCrest GC & Preserve | 5&4 | Tavistock CC |
| 2015 | Kyle Vance | GAP Junior Players Club | Max Siegfried | Aronimink GC | 4&2 | Indian Valley CC |
| 2014 | Mariano Medico | Fox Hill CC | Nicolas McCook | Applecross CC | 3&2 | Riverton CC |
| 2013 | Roland Massimino | The Ridge at Back Brook | Kevin Kramarski | Riverton CC | 6&5 | The Ridge at Back Brook |
| 2012 | Mariano Medico | Fox Hill CC | Evan Thornton | Berkshire CC | 1-up | Torresdale-Frankford CC |
| 2011 | Brandon Matthews | Fox Hill CC | Reilly Erhardt | Trenton CC | 1-up | Running Deer GC |
| 2010 | Vince Boyle | Torresdale-Frankford CC | Benjamin Cooley | Lu Lu CC | 1-up | Whitford CC |
| 2009 | Zachary Herr | Jericho National GC | James Tallent | Merion GC | 19 holes | Riverton CC |
| 2008 | Robert Galbreath, Jr. | Huntingdon Valley CC | Russell Hartung | Doylestown CC | 4&2 | Huntingdon Valley CC (Centennial/Flynn) |
| 2007 | Robert Galbreath, Jr. | Huntingdon Valley CC | Robert Robertson | Sunnybrook GC | 1-up | Cavaliers CC |
| 2006 | Matt Raudenbush | Pine Valley GC | Michael Kania | Overbrook GC | 2&1 | Philadelphia CC |
| 2005 | Robert Galbreath, Jr. | Huntingdon Valley CC | Amory Davis | DuPont CC | 1-up | Torresdale-Frankford CC |
| 2004 | Robert Galbreath, Jr. | Philmont CC | James Kania, Jr. | Overbrook GC | 1-up | Philmont CC (South) |
| 2003 | Kyle Davis | Kennett Square G&CC | Billy McCrossan | The Springhaven Club | 20 holes | Bala GC |
| 2002 | John Sawin | Philadelphia CC | Ryan McCarty | Little Mill CC | 20 holes | Running Deer GC |
| 2001 | Billy Stewart | Llanerch CC | Christian Davis | Glenmaura National GC | 6&5 | Downingtown CC |
| 2000 | Billy Stewart | Llanerch CC | Vince Covello | Llanerch CC | 2&1 | Huntingdon Valley CC |
| 1999 | Meredith Henry, Jr. | Stone Harbor GC | Dan Levy | Philmont CC | 4&3 | Downingtown CC |
| 1998 | Sam McFall | Waynesborough CC | Benjamin Levy | Philmont CC | 1-up | Whitford CC |
| 1997 | Joseph Glynn | Llanerch CC | Kurt Hirsekorn | Tavistock CC | 3&2 | McCall Field CC |
| 1996 | Graham Wilson | Kennett Square G&CC | Christian Bartolacci | Yardley CC | 20 holes | Kennett Square G&CC |
| 1995 | Jon Rusk | Yardley CC | Chris Roselle | Overbrook GC | 7&5 | Meadowlands CC |
| 1994 | Sal Paone | Cedarbrook CC | Carl Greener | Lehigh CC | 4&3 | McCall Field CC |
| 1993 | Aaron Friedman | Meadowlands CC | Scott Larsen | Whitford CC | 1-up | Cedarbrook CC |
| 1992 | Chris Hoyle | Llanerch CC | Sean Coyle | Llanerch CC | 4&3 | Merion GC (West) |
| 1991 | Brad McFadden | Overbrook GC | Chris Hoyle | Llanerch CC | 1-up | Overbrook GC |
| 1990 | Brad McFadden | Overbrook GC | Matt Shevlin | North Hills CC | 7&6 | Philadelphia Electric CC |
| 1989 | Eric Dollenberg | Philadelphia Cricket Club | Tom Fluehr | Torresdale-Frankford CC | 5&4 | Ashbourne CC |
| 1988 | Chris Yard | Whitford CC | Scott Shore | Aronimink GC | 6&4 | Philadelphia Electric CC |
| 1987 | Jeff Craig | Radley Run CC | Greg Fieger | The Springhaven Club | 3&2 | Radley Run CC |
| 1986 | Kevin Walsh | Huntingdon Valley CC | Tom Murphy | Radley Run CC | 3&2 | Huntingdon Valley CC |
| 1985 | Tom Feeney | Chester Valley GC | William Hyndman, V | Huntingdon Valley CC | 1-up | Meadowlands CC |
| 1984 | Doug Gregor | Torresdale-Frankford CC | Steve Turner | Sandy Run CC | 4&3 | Philmont CC |
| 1983 | John Sweeney | Trenton CC | Jim Anderson | Trenton CC | 3&2 | Kennett Square G&CC |
| 1982 | Neil Ahearn | Trenton CC | Brian Stefanowicz | Torresdale-Frankford CC | 2&1 | Torresdale-Frankford CC |
| 1981 | Erik Hagar | Waynesborough CC | Richard Gregor | Torresdale-Frankford CC | 1-up | Waynesborough CC |
| 1980 | Chris Fieger | The Springhaven Club | Brian Stefanowicz | Torresdale-Frankford CC | 5&3 | Doylestown CC |
| 1979 | Todd Anderson | Wilmington CC | Miguel Biamon | Saucon Valley CC | 2&1 | Llanerch CC |
| 1978 | Dave Ellsworth | DuPont CC | Dave Roberts | Saucon Valley CC | 19 holes | DuPont CC |
| 1977 | Steve Loughran | Philadelphia Cricket Club | Tom Harman | Wilmington CC | 1-up | Philadelphia Cricket Club |
| 1976 | Bruce Whiteford | Tavistock CC | Steve Loughran | Philadelphia Cricket Club | 1-up | Torresdale-Frankford CC |
| 1975 | John F. Peterson | Riverton CC | E. Michael Forgash | Waynesborough CC | 4&3 | Philmont CC (South) |
| 1974 | E. Michael Forgash | Waynesborough CC | Michael Stanley | St. Davids GC | 1-up | St. Davids GC |
| 1973 | Mark W. Curlett | Coatesville CC | John Trickett, Jr. | Aronimink GC | 5&4 | Chester Valley GC |
| 1972 | Chip Lutz | Berkshire CC | Robert Drygas | Sandy Run CC | 1-up | Radley Run CC |
| 1971 | Bob Dorsey | Medford Lakes CC | Bruce Disbrow | Moorestown FC | 4&3 | Waynesborough CC |
| 1970 | Bob Dorsey | Medford Lakes CC | Samuel Forese, II | Coatesville CC | 20 holes | Coatesville CC |
| 1969 | Donald DeAngelis | Plymouth CC | Richard C. Osberg | Hercules CC | 22 holes | Whitford CC |
| 1968 | Steven Marshall | Huntingdon Valley CC | Richard Langille | Riverton CC | 2&1 | Huntingdon Valley CC |
| 1967 | Eric Stevenson | Plymouth CC | John Stoviak | Whitford CC | 1-up | Plymouth CC |
| 1966 | Edward E. Marshall, III | Huntingdon Valley CC | Ted Hagedorn | Old York Road CC | 5&3 | Llanerch CC |
| 1965 | Andy Thompson | Overbrook GC | Donald Strieger | DuPont CC | 4&3 | Overbrook GC |
| 1964 | Thomas Apple | Indian Valley CC | Michael Rowland | Brookside CC | 2&1 | Brookside CC |
| 1963 | William “Trip” O’Donnell, III | Brookside CC | Michael Rowland | Brookside CC | 4&3 | Brookside CC |
| 1962 | Thomas Hyndman | Huntingdon Valley CC | William “Trip” O’Donnell, III | Brookside CC | 2&1 | Huntingdon Valley CC |
| 1961 | Stephen Probst | Manufacturers' G&CC | William “Trip” O’Donnell | Brookside CC | 4&3 | Plymouth CC |
| 1960 | Robert McMahon | Whitemarsh Valley CC | R. Jay Sigel | Bala GC | 6&5 | St. Davids GC |
| 1959 | Robert McMahon | Whitemarsh Valley CC | R. Jay Sigel | Bala GC | 1-up | St. Davids GC |
| 1958 | Norman Patrich | Woodcrest CC | David King | St. Davids GC | 3&2 | St. Davids GC |
| 1957 | William H. Care | Atlantic City CC | Edward DeBaufre | Wildwood CC | 5&4 | St. Davids GC |
| 1956 | Robert Lindinger | St. Davids GC | William Hyndman, IV | Huntingdon Valley CC | 5&3 | St. Davids GC |
| 1955 | Rodman Zwirner, Jr. | Riverton CC | Harry Elwell, III | Atlantic City CC | 6&4 | St. Davids GC |
| 1954 | W.B. McCullough, III | Huntingdon Valley CC | Gibson Smith | Lehigh CC | 6&5 | St. Davids GC |
| 1953 | Gibson Smith | Lehigh CC | Charles Ehresman | Ashbourne CC | | Sandy Run CC |
| 1952 | Edwin C. Vare | Philadelphia CC | William Houldin, Jr. | Old York Road CC | 4&3 | Merion GC |
| 1951 | James D. Sykes | Old York Road CC | Francis Poore | Whitemarsh Valley CC | 1-up | Huntingdon Valley CC |
| 1950 | William J. Albertus | Overbrook GC | Thomas Conboy | Whitemarsh Valley CC | 1-up | Tully-Secane CC |
| 1949 | Fred Phillips | Merion GC | Lincoln Roden, III | Huntingdon Valley CC | 3&2 | Philadelphia Cricket Club |
| 1948 | Robert J. Baldorf | Berkshire CC | John Fraser | Old York Road CC | 1-up | Rolling Green GC |
| 1947 | J. Elmer Lutz, Jr. | Reading CC | Charles R. Hoffner, Jr. | Melrose CC | 2-up | Philadelphia Cricket Club |
| 1946 | Jacques Houdry | Merion GC | J. Elmer Lutz, Jr. | Reading CC | | Lu Lu Temple CC |
| 1945 | Charles R. Hoffner, Jr. | Melrose CC | Louis G. Graff, III | Lu Lu Temple CC | 4&3 | Cedarbrook CC |
| 1944 | Charles J. Albertus, Jr. | Overbrook GC | Don Weiland | Phoenixville CC | | Old York Road CC |
| 1943 | No contest — World War II |
| 1942 | Charles Heuer | Old York Road CC | Frank W. Coar, Jr. | Cedarbrook CC | 8&7 | Old York Road CC |
| 1941 | John Markel | Berkshire CC | Horace Suplee, III | Cedarbrook CC | 3&2 | Cedarbrook CC |
| 1940 | John Markel | Berkshire CC | John E. Sullivan | North Hills CC | 19 holes | Lu Lu Temple CC |
| 1939 | Dennis Coltart | Roxborough CC | William Goldthrop | Woodcrest CC | 19 holes | Overbrook GC |
| 1938 | George K. Glover, Jr. | Pennsylvania GC | William Lewis | Berkshire CC | 2&1 | Philmont CC |
| 1937 | Horace C. Jones, II | Gulph Mills GC | Peter Page, Jr. | Merion GC | 1-up | Merion Cricket Club |
| 1936 | John P. Schearer | Pennsylvania GC | Clarence Hackney, Jr. | Atlantic City CC | 2-up | Philadelphia Cricket Club |
| 1935 | Sidney W. Coltart | Plymouth CC | John P. Schearer | Pennsylvania GC | 1-up | Ashbourne CC |
| 1934 | H. Lloyd Beyer, Jr. | Aronimink GC | John P. Schearer | Pennsylvania GC | 1-up | Manufacturers' G&CC |
| 1933 | George Menard, Jr. | Llanerch CC | William Hyndman, III | Cedarbrook CC | 2-up | Merion Cricket Club |
| 1932 | William Hyndman, III | Cedarbrook CC | Bradford K. Cross | Huntingdon Valley CC | | Huntingdon Valley CC |
| 1931 | Richard Allman | Philmont CC | M.J. Scammell, Jr. | Trenton CC | | Cedarbrook CC |
| 1930 | Gerald McHugh | Whitemarsh Valley CC | Jack Brewer | Cedarbrook CC | | Philmont CC |
| 1929 | Harold S. Cross, Jr. | Huntingdon Valley CC | W.H. Sickels, Jr. | Llanerch CC | | Whitemarsh Valley CC |
| 1928 | Conine McEntee | Doylestown CC | H.W. Koehn, Jr. | Merion Cricket Club | | Ashbourne CC |
| 1927 | W.B. McCullough, Jr. | Huntingdon Valley CC | W.M. Swoope | Overbrook GC | | Old York Road CC |
| 1926 | Joseph S. Greene | Roxborough CC | Connie McEntee | Doylestown CC | | Cedarbrook CC |
| 1925 | Joseph S. Greene | Roxborough CC | Theodore Johnston | Green Valley CC | | Huntingdon Valley CC |
| 1924 | George W. Stevens | Huntingdon Valley CC | George Boyajian, Jr. | CC of Atlantic City | | Merion Cricket Club |
| 1923 | Kean Donnelly | Stenton CC | Joseph S. Greene | Roxborough CC | | Old York Road CC |
| 1922 | J. Winston Kindt | Old York Road CC | W.F. Beadle | Llanerch CC | | Torresdale-Frankford CC |
| 1921 | H.W. Hamill | Merion Cricket Club | W.F. Beadle | Llanerch CC | | Philmont CC |
| 1920 | R. Kent Hanson | Cedarbrook CC | G.W. Stevens | Old York Road CC | | Old York Road CC |
| 1919 | Phillip S. Corson | Plymouth CC | R. Kent Hanson | Stenton CC | | North Hills CC |
| 1918 | J. Wood Platt | North Hills CC | H.L. Newton | Frankford CC | | St. Davids GC |
| 1917 | Phillip S. Corson | Plymouth CC | C.F. Kindt, Jr. | Old York Road CC | | Philadelphia CC |
| 1916 | Meredith M. Jack | Merion Cricket Club | E.D. Stevens | Old York Road CC | | Whitemarsh Valley CC |
| 1915 | Meredith M. Jack | Merion Cricket Club | John P. MacBean | Old York Road CC | | Philadelphia CC |
| 1914 | Meredith M. Jack | Merion Cricket Club | L.M. Washburn | Merion Cricket Club | | Merion Cricket Club |
