Here is a list of Grand Silver Cup winners (Renamed the Robert DiRinaldo Grand Silver Cup in 2013) as we are aware of them. Unfortunately, SSIA's archives were damaged in a flood, so we no longer have a complete list. If you know of someone not included on the list, please forward that information to webmaster@ssia.info
| 2025 | Luke George |
| 2023 | Patrick Nijdam |
| 2021 | Martin Sugg |
| 2019 | Ronald Nijdam |
| 2017 | Steve Doudaklian |
| 2015 | Glenn DiMauro |
| 2013 | Johann Remmerts |
| 2011 | Barry Croft |
| 2008 | Peter Holmer |
| 2006 | Gino Gentile |
| 2005 | Chuck Bolinger |
| 2004 | Barry Croft |
| 2003 | Larry Schupbach |
| 2002 | Jim McFarland |
| 2001 | Jules Van Passel |
| 2000 | Delwyn Thornton |
| 1999 | Jeff Kay |
| 1998 | Bob Galvin |
| 1997 | Jean Van Passel |
| 1996 | Julio Tottil |
| 1995 | Daniel Verbruggen |
| 1994 | Rick Woodland |
| 1993 | Antonio Del Toro |
| 1992 | George Fortuna |
| 1991 | Todd Anderson |
| 1990 | No contest due to change in show schedule |
| 1989 | Jim Johnston |
| 1988 | Ken Vogt |
| 1987 | Robert DiRinaldo |
| 1986 | Raul Guayta |
| 1985 | Frank Longo |
| 1984 | Paul Krause |
| 1983 | John Janeke |
| 1982 | Charles Ross |
| 1981 | Frank Milatzo |
| 1980 | |
| 1979 | No Grand Silver Cup Awarded |
| 1978 | Charles E. Thompson |
| 1977 | Anthony & John Trani |
| 1976 | Charles Thomasson |
| 1975 | John Paul Traverso |
| 1974 | Sammy Incardona |
| 1973 | Elio Floro |
| 1972 | Charles Pignataro |
| 1971 | Ted Goto |
| 1970 | Phil Concelli |
1969 |
No Silver Cup contest as it would conflict with 22nd National Shoe Serviceman's Days out in Denver, CO 8/30 & 8/31 |
1968 |
Boris Gartner |
1967 |
|
1966 |
William M. O'Bryan |
1965 |
Henry Salzman Jr. |
1964 |
Samuel M. Coco & Carmel C. Coco |
1963 |
|
1962 |
Pasquale DiFabrizio |
1961 |
Vincent Joe Adamo |
1960 |
Donald P. Vogt |
| 1959 | Antonio Palmeri |
| 1958 | Charles Federico |
| 1957 | Larry Anthony Modica |
| 1956 | Pomeo DiPrima Sr. |
| 1955 | John Santapadre |
| 1954 | Lovell D. Warrick |
| 1953 | Joseph Santapadre |
| 1952 | Luco Liparulo |
| 1951 | Victor Zuclich |
| 1950 | Avery Gerald |
| 1949 | Emil Perruso |
| 1948 | Leon Danna |
| 1947 | |
| 1946 | |
| 1945 | No convention by order of the Department of Defense regarding Transportation |
| 1944 | |
| 1943 | |
| 1942 | |
| 1941 | |
| 1940 | |
| 1939 | |
| 1938 | Eugene Melvin Goodwin |