Given in 1957 in memory of Ann Shepard Briggs Copp, the daughter of
L/ Goffe and Sallie Lee Briggs, former MIYC members, and the sister of
current MIYC member Patty Copp and Past Commodore Peter Briggs.
Awarded to the cumulative winner of a series of
racing starts, customarily held around the Labor Day weekend.
| 1958 | R.W. Halsey, Jr | 1985 | Martin Lyons | ||
| 1959 | H.M. Smith IV | 1986 | Duncan Henderson | ||
| 1960 | Robert P. Rowe, Jr. | 1987 | L.B. (Bos) Powell | ||
| 1961-1962 | R.W. Halsey, Jr. | 1989 | Morgan Connor | ||
| 1963 | M.W. Williams, Jr. | 1990 | Karin Soderberg | ||
| 1964 | Hugh Cole | 1991 | Peter Canning | ||
| 1965 | H.M. Smith IV | 1992 | Grant Stuart | ||
| 1967 | Hunter Townsend | 1993 | Peter Briggs | ||
| 1968 | Hugh Cole | 1995 | H.M. Smith IV | ||
| 1969 | Stephen H. Haig | 1996 | Peter Briggs | ||
| 1970 | Susie Attwood, Patty Humphrey | 1997- 1999 | Kaitlin & Jeffrey Parry | ||
| 1971 | Stephen H. Haig | 2000 | Goffe Briggs II | ||
| 1972 | Duncan Y. Henderson | 2001 – 2002 | Anthony Parr, Cody Williams | ||
| 1973 | L. B. Moore | 2003 – 2004 | Peter Augusciak | ||
| 1974 | Andy Hallberg | 2006 | Max Plummer | ||
| 1975 | Susie & Polly Attwood | 2007 | Caroline Canning | ||
| 1976 | Scott Parry | 2008 | Jack Hisle | ||
| 1977 | Mark C. Briggs | 2009 | Caroline Canning | ||
| 1978 | Scott Parry | 2010 | John Clark | ||
| 1980 | Mark Leibig | 2013 | Libby Stuart | ||
| 1981 | Hugh Cole, Jr. | 2014 | Gabrielle Nafie | ||
| 1982 | Billie Palmer | 2015 | Katherine Glenn | ||
| 1983 | Norman Anderson | 2017- 2019 | Not held | ||