SM Sailing Junior Championship (Cumming Cup)
In the year 1930, Commodore Robert W. Cumming of the Beverly Yacht Club presented the Cumming Cup,a trophy to be awarded to the crew from a member Yacht Club of SM Sailing that attains the lowest point score in the district finals for the National Junior Championship. The names of the members of the winning crew, together with the name of the Yacht Club they represented and the year, are engraved upon the permanent trophy. The numbers of the winning crew each receive suitable mementos.
Crew of three including skipper in Flying Scots
Each club may enter one (1) boat for this event. Member club dues must be paid prior to this event.
| Date | Club | Skipper |
| 2023 | ||
| 2020-2022 | No Contests | Cancelled due to Covid/lack of Interest |
| 2019 | Chatham Yacht Club | Will Bailey, Hank Bailey, Calder Robbins - 2019 Report |
| 2018 | Chatham Yacht Club | Ellen Fuller, Izzy Maggioni, Hank Bailey - 2018 Report |
| 2017 | Stone Horse Yacht Club | Brian Mitchell, Drew Kelly, Owen Ward - 2017 Report |
| 2016 | Stone Horse Yacht Club | Owen Ward, Marion, leMay, James McAvoy - 2016 Report |
| 2015 | Stage Harbor Yacht Club | Parker Loftus, Olivia Gonzalez, Jake Cummings - 2015 Report |
| 2014 | Stone Horse Yacht Club | Carter Mitchell, Connor McAvoy, Brad Kelly - 2014 Report |
| 2013 | Wianno Yacht Club | Chase Quinn, JP Cannistraro, and Will Cannistraro - 2013 Report |
| 2012 | Cotuit Mosquito Yacht Club | John Keally, Andrew Solomon, Nick Solomon - 2012 Report |
| 2011 | Grand Cove Yacht Club | William Godfrey, Mary Kate Mezzetti, Asa Smith - 2011 Results |
| 2010 | New Bedford Yacht Club | Daniel Barry, Matt Wordell, Sean McLaughlin - 2010 Results |
| 2009 | Cotuit Mosquito Yacht Club | Pete Edmunds, Adam Keally and Samantha Nuechterlein - 2009 results |
| 2009 Regatta Report | ||
| 2008 | Vineyard Haven Yacht Club | Alexander Sutula - 2008 results |
| 2007 | Vineyard Haven Yacht Club | 2007 results |
| 2001 | Vineyard Haven Yacht Club | Seth Besse |
| 2000 | Vineyard Haven Yacht Club | Sebastian Reeve |
| 1999 | Nantucket Yacht Club | Kinloch Yellott |
| 1998 | Nantucket Yacht Club | Kinloch Yellott |
| 1997 | Duxbury Yacht Club | Jack Donahue |
| 1996 | Vineyard Haven Yacht Club | Jared Hammond |
| 1995 | Chapoquoit Yacht Club | Matt Strickland |
| 1994 | Hyannis Yacht Club | Eric Knight |
| 1993 | New Bedford Yacht Club | Chris Murray |
| 1992 | Falmouth Yacht Club | Ryan Richards |
| 1991 | Edgartown Yacht Club | Tad White |
| 1990 | Hyannis Yacht Club | Peter O'Toole |
| 1989 | Beverly Yacht Club | Sam Vineyard |
| 1988 | Duxbury Yacht Club | Carl Smit |
| 1987 | Chatham Yacht Club | John Dickson |
| 1986 | Buzzards Yacht Club | Doug Schofield |
| 1985 | Stage Harbor Yacht Club | Peter Mottur |
| 1984 | Wild Harbor Yacht Club | Michael O'Connor |
| 1983 | Wianno Yacht Club | Sarah Burnes |
| 1982 | Vineyard Haven Yacht Club | Timothy F. Colen |
| 1981 | Wianno Yacht Club | Stephen Ulian |
| 1980 | Wianno Yacht Club | Stephen Ulian |
| 1979 | Vineyard Haven Yacht Club | Geoff Cassel |
| 1978 | Hyannis Port Yacht Club | William Curley, Jr. |
| 1977 | Vineyard Haven Yacht Club | Nevin Sayre |
| 1976 | Stage Harbor Yacht Club | Carl Lindegren |
| 1975 | Vineyard Haven Yacht Club | Peter Howell |
| 1974 | Vineyard Haven Yacht Club | Paul L. Duane |
| 1973 | Woods Hole Yacht Club | Stephen Strittmatter |
| 1972 | Vineyard Haven Yacht Club | Paul L. Duane |
| 1971 | Stage Harbor Yacht Club | Richard Hoyt |
| 1970 | Stage Harbor Yacht Club | Thomas Lewit |
| 1969 | Vineyard Haven Yacht Club | Charles D. Duane |
| 1968 | Wianno Yacht Club | John C. Kiley, III |
| 1967 | Wianno Yacht Club | John C. Kiley, III |
| 1966 | Vineyard Haven Yacht Club | Stephen Besse |
| 1965 | Vineyard Haven Yacht Club | Stephen Besse |
| 1964 | Vineyard Haven Yacht Club | Stephen Besse |
| 1963 | Hyannis Port Yacht Club | Charles E. Loutrel, Jr. |
| 1962 | Beverly Yacht Club | John Cunningham, Jr. |
| 1961 | Hyannis Port Yacht Club | Charles E. Loutrel, Jr. |
| 1960 | Edgartown Yacht Club | Peter Plumb |
| 1959 | Edgartown Yacht Club | Nancy B. Blair |
| 1958 | Edgartown Yacht Club | Nancy B. Blair |
| 1957 | Chatham Yacht Club | Charles E. McClennan |
| 1956 | Stage Harbor Yacht Club | Bartlett S. Dunbar |
| 1955 | Beverly Yacht Club | Albert R. Pierce, III |
| 1954 | Beverly Yacht Club | Albert R. Pierce, III |
| 1953 | Buzzards Yacht Club | Talbot Baker, Jr. |
| 1952 | Vineyard Haven Yacht Club | Mary Scott |
| 1951 | Chatham Yacht Club | Charles Leighton |
| 1950 | Edgartown Yacht Club | Martin N. Morey |
| 1949 | Vineyard Haven Yacht Club | Douglas Cassel |
| 1948 | Vineyard Haven Yacht Club | Douglas Cassel* |
| 1947 | Buzzards Yacht Club | Michael Jackson* |
| 1946 | Stage Harbor Yacht Club | William R. Maclay* |
| 1943-1945 | No Contests | |
| 1942 | Vineyard Haven Yacht Club | John H. Mills |
| 1941 | Vineyard Haven Yacht Club | John H. Mills |
| 1940 | Vineyard Haven Yacht Club | John H. Mills |
| 1939 | Lewis Bay Yacht Club | Nancy Syme |
| 1938 | Cotuit Mosquito Yacht Club | Frederick Platt |
| 1937 | Vineyard Haven Yacht Club | Arthur Besse, Jr. |
| 1936 | Vineyard Haven Yacht Club | John H. Ware* |
| 1935 | Vineyard Haven Yacht Club | John H. Ware* |
| 1934 | Vineyard Haven Yacht Club | Frank B. Jewet, Jr.* |
| 1933 | Vineyard Haven Yacht Club | Frank B. Jewet, Jr.* |
| 1932 | Vineyard Haven Yacht Club | Frank B. Jewet, Jr. |
| 1931 | Beverly Yacht Club | Michael Cudahy* |
| 1930 | Vineyard Haven Yacht Club | William S. Cox* |
*Denotes winner of Sears Cup