Wianno Yacht Club Long Distance Race
Race Winners
| Year | Yacht | Skipper |
| 1916 | Fantasy | James G. Hinkle |
| 1917 | No Record | |
| 1918 | Ethyl | Melville |
| 1919 | No Record |
Long Distance Challenge Cup
Presented by Commodore Edward C. Crossett
(Trophy Retired by James G. Hinkle)
| Year | Yacht | Skipper |
| 1920 | A.P.H. | W.P. Halliday |
| 1921 | Fantasy | James G. Hinkle |
| 1922 | Tomboy | Edward C. Crossett |
| 1923 | Fantasy | James G. Hinkle |
| 1924 | Wendy | Henry B. Day |
| 1925 | Water Nymph | Fritz B. Talbot |
| 1926 | A.P.H. | W.P. Halliday |
| 1927 | Tomboy | Edward C. Crossett |
| 1928 | Ethyl | Robert M. Roloson |
| 1929 | Wendy | Henry B. Day |
| 1930 | Malolo | Harry F. Stimpson |
| 1931 | Malolo | Harry F. Stimpson |
| 1932 | Tomboy | Edward C. Crossett |
| 1933 | Venture | David D. Steere |
| 1934 | Gull | C. McGregory Wells |
| 1935 | Moby Dick | William R. Scott |
| 1936 | Quip | Mrs. Kenneth Boyd |
| 1937 | Fiddler | Mary Parlett |
| 1938 | Jolly Roger | James A. Waller |
| 1939 | El Cid II | John C. Kiley, Jr. |
| 1940 | Jivaro | P. & D. Bauder |
| 1941 | Cave Canum | Joseph P. Carney |
| 1941-1945 | No Races | |
| 1946 | Fantasy | James G. Hinkle |
‘Tween Waters Trophy
Presented by Commodore John W. Hornor
(Retired by John C. Kiley, Jr.)
| Year | Yacht | Skipper |
| 1947 | El Cid II | John C. Kiley, Jr. |
| 1948 | Commy | John Shafroth |
| 1949 | West Wind | W.W. Sinclaire |
| 1950 | El Cid II | John C. Kiley, Jr. |
| 1951 | Kypris | Joseph Mattison, Jr. |
| 1952 | Kypris | Joseph Mattison, Jr. |
| 1953 | Ruweido VII | Gordon R. Beggs |
| 1954 | El Cid II | John C. Kiley, Jr. |
| 1955 | Fire Chief | Vincent R. Bailey |
| 1956 | Commy | John Shafroth |
| 1957 | Bettayet | Ross Richards |
| 1958 | Dungolphin | Durban McGraw |
| 1959 | Marna | John T. Fallon |
| 1960 | Bettayet | Ross Richards |
| 1961 | No Record | |
| 1962 | Venture | David D. Steere |
| 1963 | Sovereign | Harrison Bridge |
| 1964 | Venture | David D. Steere |
| 1965 | Venture | David D. Steere |
| 1966 | Victura | Edward M. Kennedy |
| 1967 | Venture | David D. Steere |
| 1968 | Invader | Lewis J.H. Gunn |
| 1969 | No Record | |
| 1970 | Venture | David D. Steere |
| 1971 | No Record | |
| 1972 | Kialoa | John C. Kiley, III |
| 1973 | No Record | |
| 1974 | Pertelote | Boardman Lloyd |
| 1975 | Pertelote | Francis V. Lloyd, III |
| 1976 | Invader | Lewis J.H. Gunn |
| 1977-1978 | No Record | |
| 1979 | Pertelote | Boardman Lloyd |
| 1980 | Cirrus | Alden Edmonds |
| 1981 | No Record | |
| 1982 | Pertelote | Boardman Lloyd |
| 1983-1985 | No Record | |
| 1986 | Molly | Alan T. McDonough |
| 1987 | Victura | Edward M. Kennedy |
| 1988 | Cirrus | Holly Edmonds |
James G. Hinkle Long Distance Trophy
1920 Crossett Trophy Placed Back in Competition by the Hinkle Family
| Year | Yacht | Skipper |
| 1989 | Cochenoe | Andrew Pesek |
| 1990 | Marna | John T. Fallon, Jr. |
| 1991 | Invader | Lewis J.H. Gunn |
| 1992 | Invader | Lewis J.H. Gunn |
| 1993 | Fantasy | Joseph D. Hinkle |
| 1994 | Fantasy | Joseph D. Hinkle |
| 1995 | Molly | John T. McDonough |
| 1996 | Escapade | Barry Plunkett, Jr. |
| 1997 | Cirrus | Holly Edwards |
| 1998 | Chanzia | Lloyd B. McManus, Jr. |
| 1999 | Molly | John T. McDonough |
| 2000 | Yankee Dime | Alden Edmonds |
| 2001 | Lucinda | Chip Niehoff |
| 2002 | Cochenoe | Donald F. Law, Jr. |
| 2003 | Lindy | David McDonough |
| 2004 | Dauntless | Jeffrey Tracy |
| 2005 | Aurora | Karl Anderson |
| 2006 | Dauntless | Jeffrey Tracy |
| 2007 | Mad Jack | Jack Hamilton |
| 2008 | Mad Jack | Jack Hamilton |
| 2009 | Pieces of 8 | John Gregg |
| 2010 | Smoke | Joe Lotuff |
| 2011 | No Race | High Winds |
| 2012 | Aurora | Matt Cannistraro |
| 2013 | Beltane | Jim Cunningham |
| 2014 | Mad Jack | Jack Hamilton |
| 2015 | Eowyn | Timothy Wadlow |
| 2016 | Mad Jack | Jack Hamilton |
| 2017 | Scout | Sophie Pesek |
| 2018 | Eowyn | Tim Wadlow |
| 2019 | Mad Jack | Jack Hamilton |
| 2020 | Not sailed | Covid-19 Pandemic |
| 2021 | Novanglus | Greg Dempsey |
| 2022 | Three Sticks | Peter McAvoy |