Presented in 1962 by members of the Club in honor of Mr. William C. B. Roberts. The award is made annually to the member of the Junior Program who has shown the most interest in sailing as evidenced by enthusiasm, improvement in sailing techniques, awareness of the rules of water safety, and cooperation with the members of the Junior Activities program. The selection shall be made by a committee chaired by the Junior Program chairman.
| 1962 | Andrew H. Sinnickson | |
| 1963 | Thomas S. Call | |
| 1966 | Lucy McCullough | |
| 1967 | John Ogden, Jr. | |
| 1968 | George Prout, III | |
| 1969 | Lewis Toms | |
| 1970 | Beth Haymes | |
| 1971 | Clare Woodley | |
| 1972 | Paul White | |
| 1973 | Tony Farrell | |
| 1974 | James Lorimer | |
| 1975 | Richard Harding | |
| 1976 | Nick Gander | |
| 1977 | Johnny Anderson | |
| 1978 | John Hubbard | |
| 1979 | Jeff Nelson | |
| 1980 | Ross Hamilton, Jr. | |
| 1981 | Richard Jones | |
| 1982 | Louise Jones | |
| 1983 | Harrison Hubard | |
| 1984 | Tripp Davis | |
| 1985 | Caroline Collins | |
| 1986 | Damno Wright | |
| 1987 | Robert Jones | |
| 1988 | Clark Dennison | |
| 1989 | Carrington Guy | |
| 1990 | Scott Collins | |
| 1991 | Stephanie Clough | |
| 1992 | Ryan Jones | |
| 1993 | Blair Hamilton | |
| 1994 | Will Hamilton & Addison Thompson | |
| 1995 | Anna Cobb & Jennifer Celesia | |
| 1996 | Chris Hamilton | |
| 1997 | Blake Kimbrough | |
| 1998 | Alex O'Toole | |
| 1999 | Lucy Kupersmith | |
| 2000 | Justin Wilton | |
| 2001 | Anna MacKinnon | |
| 2002 | Meg Roberts | |
| 2003 | Madeleine Alderman | |
| 2004 | Sophie Massie & Kyle Swenson | |
| 2005 | Daniel Bagbey | |
| 2006 | Graeme Alderman | |
| 2007 | Conrad Roos | |
| 2008 | Erin Jacob | |
| 2009 | Banjamin Buhl | |
| 2010 | Jed Londrey & Eric Roos | |
| 2011 | Trent Levy | |
| 2012 | Luke Hayes | |
| 2013 | Eric Roos | |
| 2014 | Eric Roos | |
| 2015 | Luke Hayes | |
| 2016 | Ralph Levy & Jordan Bendura | |
| 2017 | Morey Levy | |
| 2018 | Charlotte Patterson | |
| 2019 | Charlotte Patterson | |
| 2020 | Opti: Stephen Utley, ILCA: Josh Bendura, c420: Georgia Wensell & Charlotte Staas | |
| 2021 | Opti: Alec Berg, ILCA: John Thomas Mason, c420: Anne-Kinsey Wash & Charlotte Staas | |
| 2022 | Opti: Cyrus Garrett, ILCA: Josh Almany, c420: Justinas Petkauskas & Madeleine Garrett | |
| 2023 | Opti: Sebastian Angus, ILCA: William Sutten, c420: Justinas Petkauskas & Madeleine Garrett |