| 2023 | No contest
|
| 2022 | No contest - Lack of entries
|
| 2021 | Davis Conaway | Fieldstone GC | Sean Curran | Merion GC | 20 holes | Moorestown Field Club |
| 2020 | J.P. Hoban | McCall GC | Jax Puskar | Kennett Square G&CC | 3&2 | West Chester G&CC |
| 2019 | Jack Homer | Wilmington CC | Sean Curran, Jr. | Merion GC | 1-up | Flourtown CC |
| 2018 | Benjamin Saggers | Applecross CC | Matthew Homer | Wilmington CC | 4&3 | Merchantville CC |
| 2017 | Josh Ryan | Lu Lu CC | Ben Saggers | Applecross CC | 2&1 | Phoenixville CC |
| 2016 | Brett McGrath | Huntingdon Valley CC | Roy Anderson | Kennett Square G&CC | 7&5 | Moorestown Field Club |
| 2015 | Louis John Giovi | Mercer Oaks GC | Patrick Isztwan | Huntingdon Valley CC | 1-up | West Chester G&CC |
| 2014 | Case Hummer | Aronimink GC | Frankie Gregor | Huntingdon Valley CC | 19 holes | Flourtown CC |
| 2013 | Colman Mitchell | Wilmington CC | Phillip Bancroft, III | Trenton CC | 2&1 | Merchantville CC |
| 2012 | Nate Menon | LedgeRock GC | Lukas Clark | Jericho National GC | 6&5 | Phoenixville CC |
| 2011 | R.J. Wren | Honeybrook GC | Jake Fazio | Huntingdon Valley CC | 7&5 | Moorestown Field Club |
| 2010 | Kevin Conners, Jr. | Whitford CC | Jack Quirk | Huntingdon Valley CC | 2&1 | West Chester G&CC |
| 2009 | Cole Berman | Philadelphia Cricket Club | Brock Kovach | Berkshire CC | 6&5 | Merchantville CC |
| 2008 | Zachary Herr | Jericho National GC | Brendan Papariello | White Manor CC | 5&4 | Phoenixville CC |
| 2007 | Zach Dilcher | Hartefeld National | Alex Kane | Radley Run CC | 2-up | Moorestown Field Club |
| 2006 | Jonathan Ortiz | Philmont CC | Zach Dilcher | Hartefeld National | 4&2 | Woodbury CC |
| 2005 | Zach Dilcher | Inniscrone GC | Edward McCrossen, Jr. | Whitemarsh Valley CC | 20 holes | West Chester G&CC |
| 2004 | Michael Kania | Overbrook GC | Patrick Welsh | Huntingdon Valley CC | 4&3 | Merchantville CC |
| 2003 | James Kania, Jr. | Overbrook GC | Christopher Allan, Jr. | Whitford CC | 2&1 | Phoenixville CC |
| 2002 | Amory Davis | DuPont CC | Eric Schmehl | Moorestown Field Club | 2-up | Moorestown Field Club |
| 2001 | Craig Tallent | Merion GC | Christopher Allan, Jr. | Whitford CC | 4&2 | Downingtown CC |
| 2000 | Eli Perry | Talamore at Oak Terrace | Patrick Marshalek | Whitford CC | 6&4 | Huntingdon Valley CC |
| 1999 | Jamie Wallace | Moorestown Field Club | Chris Reedman | Trenton CC | 22 holes | Downingtown CC |
| 1998 | Mark Zbrzeznj | Whitemarsh Valley CC | Nathan Shevchik | Whitford CC | 1-up | Whitford CC |
| 1997 | Dan Levy | Philmont CC | Robert Ockenfuss, Jr. | Indian Valley CC | 2&1 | McCall Field CC |
| 1996 | Jonathan Ross | Gulph Mills GC | William Weihenmayer, Jr. | Huntingdon Valley CC | 2&1 | Kennett Square G&CC |
| 1995 | Eric Pearson, Jr. | Philadelphia Cricket Club | Brad Bathgate | Huntingdon Valley CC | 6&5 | Meadowlands CC |
| 1994 | Greg Marshalek | Whitford CC | William Sicks | Philadelphia Cricket Club | 5&4 | McCall Field CC |
| 1993 | Peter J. Kent | Overbrook GC | Michael Goldman | Philmont CC | 1-up | Cedarbrook CC |
| 1992 | Brian Thompson | Overbrook GC | Andrew Strock | Yardley CC | 6&5 | Merion GC (West) |
| 1991 | Danny Duffy | Trenton CC | Michael Schanne, Jr. | Rolling Green GC | 6&5 | Overbrook GC |
| 1990 | Jeffrey Burger | Melrose CC | Kevin Bondi | Huntingdon Valley CC | 3&1 | Philadelphia Electric Club |
| 1989 | Sean Messano | Cavaliers CC | Jeff Larsen | Whitford CC | 2&1 | Ashbourne CC |
| 1988 | Scott Larsen | Whitford CC | Brad McFadden | Overbrook GC | 6&5 | Philadelphia Electric Club |
| 1987 | Scott Larsen | Whitford CC | Brad McFadden | Overbrook GC | 3&2 | Radley Run CC |
| 1986 | Eric Dollenberg | Manufacturers' G&CC | Stuart Katzoff | Philmont CC | 3&2 | Huntingdon Valley CC |
| 1985 | Eric Dollenberg | Manufacturers' G&CC | Stuart Katzoff | Philmont CC | 2-up | Meadowlands CC |
| 1984 | Greg Fieger | The Springhaven Club | Brian Sawyer | Atlantic City CC | 8&7 | Philmont CC |
| 1983 | Kieran Cunniffe | Medford Lakes CC | Greg Fieger | The Springhaven Club | 1-up | Kennett Square G&CC |
| 1982 | Tomm Feeney | Llanerch CC | Ed Stein | Torresdale-Frankford CC | 6&4 | Torresdale-Frankford CC |
| 1981 | Gregg Hagar | Waynesborough CC | Doug Gregor | Torresdale-Frankford CC | 4&3 | Waynesborough CC |
| 1980 | Steve Chaplin | Brookside CC | John Sweeney | Trenton CC | 6&5 | Doylestown CC |
| 1979 | Roger Roberts | Saucon Valley CC | Brian Slowey | Saucon Valley CC | 3&2 | Llanerch CC |
| 1978 | Roger Roberts | Saucon Valley CC | Chris Savage | Torresdale-Frankford CC | 1-up | DuPont CC |
| 1977 | Lee Gallagher | Whitemarsh Valley CC | Scott Reynier | Brookside CC | 6&5 | Philadelphia Cricket Club |
| 1976 | Adam Stefanowicz, Jr. | Torresdale-Frankford CC | Peter Dever, Jr. | Brookside CC | 5&4 | Torresdale-Frankford CC |
| 1975 | Bill Long | Kennett Square G&CC | Miguel L. Biamon | Saucon Valley CC | 4&3 | Philmont CC (South) |
| 1974 | Richard H. Price, III | Radley Run CC | Tom Slowey | Saucon Valley CC | 2&1 | St. Davids GC |
| 1973 | Chris Terebesi | Chester Valley GC | Paul LaNoce | Plymouth CC | 3&1 | Chester Valley GC |
| 1972 | Paul LaNoce | Plymouth CC | Jake Gebret | Wilmington CC | 3&1 | Radley Run CC |
| 1971 | Jim Robertson | Llanerch CC | Matthew T. Walsh | Philadelphia CC | 3&2 | Waynesborough CC |
| 1970 | Gary Hertzler | Torresdale-Frankford CC | Jim Robertson | Llanerch CC | 5&3 | Coatesville CC |
| 1969 | Mark Curlett | Coatesville CC | Lyle McCoy | Plymouth CC | 4&3 | Whitford CC |
| 1968 | Mark Curlett | Coatesville CC | Michael Gibson | Huntingdon Valley CC | 2-up | Huntingdon Valley CC |
| 1967 | Donald Rozday | West Chester G&CC | Chip Lutz | Reading CC | 5&4 | Plymouth CC |
| 1966 | Stephen Lange | Overbrook GC | Andy Davis, Jr. | Merion GC | 5&3 | Llanerch CC |
| 1965 | Ray Thompson | Overbrook GC | Steven Marshall | Huntingdon Valley CC | 3&2 | Overbrook GC |
| 1964 | Patrick Nilon | The Springhaven Club | Ray Thompson | Overbrook GC | 11 holes | Brookside CC |
| 1963 | Douglas Fraser | Atlantic City CC | Dave Billger | Schuylkill CC | 2-up | Brookside CC |
| 1962 | Douglas Fraser | Atlantic City CC | Louis Russo | Torresdale-Frankford CC | 1-up | Huntingdon Valley CC |
| 1961 | Andy Thompson | Overbrook GC | Douglas Fraser | Atlantic City CC | 2&1 | Plymouth CC |
| 1960 | John Hoffner, Jr. | Overbrook GC | Paul Russo | Torresdale-Frankford CC | 4&3 | Torresdale-Frankford CC |
| 1959 | Phillip Keidel, Jr. | Manufacturers' G&CC | Paul Russo | Torresdale-Frankford CC | 13 holes | St. Davids GC |
| 1958 | Sam Phillips | St. Davids GC | James Fraser | Atlantic City CC | 2&1 | St. Davids GC |
| 1957 | James Fraser | Atlantic City CC | Robbie Bradley | Philadelphia Cricket Club | 2&1 | St. Davids GC |
| 1956 | Stephen Probst | Manufacturers' G&CC | John Capers, Jr. | Merion GC | 1-up | St. Davids GC |
| 1955 | Loren E. Hale | Philadelphia CC | W. Seldon Gates | Old York Road CC | St. Davids GC |
| 1954 | Loren E. Hale | Philadelphia CC | W. Seldon Gates | Old York Road CC | 4&2 | St. Davids GC |
| 1953 | John Hutchison | Saucon Valley CC | Norman Patrick | Woodcrest CC | Sandy Run CC |
| 1952 | Jay Davis | Merion GC | David Watson | Melrose CC | 5&4 | Merion GC (West) |
| 1951 | Jeff Dando | Manufacturers G&CC | Frank Ventura | Plymouth CC | 1-up | Huntingdon Valley CC |
| 1950 | Rodman Swirner | Riverton CC | Frank Ventura | Plymouth CC | Tully-Secane CC |
| 1949 | Mike Houldin | Old York Road CC | Frank Ventura | Plymouth CC | 11 holes | Philadelphia Cricket Club |
